5-Chemistry-Biochemistry-Drug

drug in chemistry

Compounds {drug, chemistry} {drug-like compound} can metabolize with biological molecule.

size

Drugs have molecular weight 200 to 700.

side effects

Drugs must have few side effects.

absorption

Body can absorb drugs.

distribution

Drugs can go to body organs and/or tissues.

metabolism

Drugs have chemical reactions at sites. Drugs have orientation at receptor site. Drugs can sterically interact with receptor site.

excretion

Drugs do not excrete too quickly.

solubility

Drugs have solubility, partition coefficients, diffusivity, and ionization degree.

variation

Drugs can vary using different salts, esters, and side groups for different sizes and surface areas.

form

Drugs can be solutions, suspensions, capsules, or tablets. They can be oral, subcutaneous, intravenous, inhaled, or patch.

history

In England, William Morton [? to 1868] used inhaled ether [1846] during surgery on October 16 (Ether Day). inhaled chloroform [1850]. inhaled nitrous oxide and oxygen [1868]. hypodermic syringe [1868]. intravenous morphine [1868]. chloral hydrate [1869]. inhaled nitrous oxide and oxygen followed by chloroform or ether [1876]. paraldehyde [1882]. cocaine [1884]. sulfones [1888]. ethyl p-aminobenzoate [1890]. Novocaine is procaine hydrochloride. Phenacetin comes from aniline by hydroxylation and conjugation [1890 to 1899]. aspirin [1899]. Anti-pyrine came from quinine [1900]. urethane [1900].

good laboratory practices

Organizations regulated by the Food and Drug Administration (FDA) are required to comply with Good Laboratory Practices {good laboratory practices} (GLP). GLP compliance requires organizations to have administrative policies, written procedures, competent personnel, and trained personnel. As part of GLP compliance, software products used in regulated organizations should comply with FDA regulations and document how compliance was achieved.

Code of Federal Regulations (CFR), Title 21, Chapter I, Part 11

Specific functions, electronic records, and auditing of software systems are required to be compliant with Code of Federal Regulations (CFR), Title 21, Chapter I, Part 11, Electronic Records; Electronic Signatures Final Rule (FDA CFR21 Part 11).

FDA CFR21 Part 11 requires accurate, reliable, and consistent software.

FDA CFR21 Part 11 does not necessarily require encryption.

FDA CFR21 Part 11 requires versioning of data and audit records.

FDA CFR21 Part 11 requires data to be entered in specific fields before processing.

FDA CFR21 Part 11 requires auditing.

FDA CFR21 Part 11 requires electronic signatures.

FDA CFR21 Part 11 has installation requirements. All necessary software components must be successfully installed and a report generated.

FDA CFR21 Part 11 has logon and logoff requirements. Systems limit access to only authorized persons, by checking user name and password. After a specific time period, automatic logoff occurs.

FDA CFR21 Part 11 has security requirements for data and audit record management, with file and operating system permissions. Attempts at unauthorized use are sent by electronic mail to the Administrator. User and user groups have privileges to files, directories, and functions. Systems can detect invalid or altered records. Auditing of user events detects creation, modification, and deletion of files, using checksums.

FDA CFR21 Part 11 requires instrument maintenance logs.

FDA CFR21 Part 11 has requirements for reporting data, parameters, and auditing information.

ADME

Drugs have absorption, distribution, metabolism, and excretion {ADME}.

ADME-PK profile

Pharmacokinetics (PK) is about absorption, distribution, metabolism, and excretion {ADME/PK profile}.

DMPK

Drug Metabolism and PharmacoKinetics {DMPK}.

excipient

Inactive chemicals {excipient}, such as solvent or powder, can carry active drugs.

human serum albumin

Plasma proteins {human serum albumin} (HSA) can carry other molecules.

pharmacodynamic drug

Drugs {pharmacodynamic drug, complex} can make complexes but not cause chemical reactions or conformational changes.

pharmacodynamics

Drugs have absorption, distribution, metabolism, and elimination {pharmacodynamics} (PD).

pharmacogenomics

Population genotypes can identify SNPs affecting drug metabolism {pharmacogenomics}.

pharmacokinetics

Absorption, distribution, metabolism, and elimination affect drugs {pharmacokinetics} (PK).

potency

High-enough concentration {potency}| causes biologic response.

prodrug

Drugs {prodrug} can require metabolization to transport or be active.

teratogenicity

Drugs can cause birth defects {teratogenicity}|, by acting on development processes.

toxicity

Drug can damage tissues {toxicity}|.

xenobiotics

Foreign compounds {xenobiotics} are vapors, alcohol, drugs, pollutants, solvents, food toxins, pesticides, and pyrolysis products. Pyrolysis products come from charring fat or protein.

5-Chemistry-Biochemistry-Drug-Activity

drug activity

Drugs have activity {drug, activity}, depending on structures and other factors.

IC50

Activity is half maximum at a concentration {IC50}.

initial activation energy

Mopac quantum-mechanical calculation can find activation energy {initial activation energy} (Ea0).

property-activity relationship

Structure can associate with physicochemical property {property-activity relationship}.

quantitative structure-activity relationship

Measured activity equals physicochemical-variable function {quantitative structure-activity relationship} (QSAR). QSAR relates activity magnitude, such as tissue concentration, to compound physico-chemical or structural property magnitudes, such as carbon-atom numbers. QSAR (3D-QSAR) can be in three dimensions.

structure-activity relationship

Activity equals physicochemical-variable function {structure-activity relationship} (SAR).

structure-property correlation

Structures and properties have relation {structure-property correlation} (SPC).

5-Chemistry-Biochemistry-Drug-Activity-Connectivity

Corey Pauling Koltun

Systems {Corey Pauling Koltun} (CPK) can display space-filling compound models.

field fit procedure

Molecule alignments can adjust {field-fit procedure}.

kappa index

Indexes {kappa index, drug} can depend on molecular shape and flexibility.

Kohonen topology-preserving mapping

Network mappings {Kohonen topology-preserving mapping} can retain topology.

Morgan algorithm

Calculations {Morgan algorithm} can make unique numberings for connection tables.

SMILES

Strings {SMILES} can uniquely describe three-dimensional structure.

substructure searching

Searches {substructure searching} can use connectivity-table parts as search criteria.

Tanimoto index

Topological indexes {Tanimoto index} can represent graphs as numbers.

topological index

Indexes {topological index} can represent graphs as numbers.

valence molecular connectivity index

Indexes {valence molecular-connectivity index} can use valence to indicate connectivity.

5-Chemistry-Biochemistry-Drug-Activity-Connectivity-Branching

branching index

Sums {branching index} over all bonds, of inverse of square root of end-atom-valence product, can measure branching amount.

molecular connectivity index

Indexes {molecular connectivity index} can depend on branching.

5-Chemistry-Biochemistry-Drug-Activity-Outliers

Dixon Q-test

Normal-distribution outlier tests {Dixon's Q-test, drug} {Dixon Q-test, drug} can measure smallest and largest difference ratio.

Grubbs s-test

Normal-distribution outlier tests {Grubbs' s-test, drug} {Grubbs s-test, drug} can compare absolute value, of difference between mean and value, divided by standard deviation, to T-distribution value.

5-Chemistry-Biochemistry-Drug-Activity-Methods

Active Analog Approach

Rules {Active Analog Approach} can align molecule activities by analogous structures.

active pharmaceutical

Rules can align molecule activities by structural group {active pharmaceutical ingredient} (API).

alternating conditional expectations

Non-parametric methods {alternating conditional expectations} (ACE) can analyze activity.

artificial neural network

Input "neuron" layer can hold physico-chemical properties and feed to middle layer using sigmoidal function {transfer function} with weights for outputs. Middle-layer "neurons" feed to one output {artificial neural network} (ANN).

chemometrics

Mathematical tools {chemometrics} applied to structure-activity relationships can find correlations and regression, recognize patterns, classify compounds and properties, design experiments for random screening and measuring, and validate results.

computer assisted metabolism prediction

Quantum mechanics can pair with empirical approaches {computer-assisted metabolism prediction} (CAMP).

deconvolution in arrays

Cell arrays can pool more than one sample in cells, which allows fewer cells. Methods {deconvolution} can track sample pooling.

convolution

Convolution puts each sample into several cells, in regular pattern. Testing looks for one effect. Some cells show effect, but most do not. If sample causes effect, all cells with that sample show effect. Cells that contain that sample form pattern, so pattern indicates sample name.

deconvolution

Deconvolution uses convolution method and resulting cell pattern to find sample name. For example, for 100-cell array, 10 samples can feed into 90 cells, each cell receiving two samples. Ten cells have control samples. See Figure 1. Samples are in 18 cells. If testing shows that all 18 have activity over threshold, then that sample is effective.

If sample interactions cause effect, deconvolution can find interactions. If testing shows that only one cell has activity over threshold, those two samples must interact to be effective.

empirical-quantum chemical

Combining quantum mechanics and physico-chemical properties {empirical-quantum chemical} {combined empirical/quantum chemical approach} can predict chemical behavior.

Korzekwa-Jones model

Models {Korzekwa-Jones model} can be for P-450 hydrogen abstraction and depend on difference between radical free energy and hydrogenated-atom free energy, as well as radical ionization potential and constant additive term.

Lennard-Jones potential

Steric effects and van der Waals forces can cause fields {Lennard-Jones potential}.

loading plot

Plots {loading plot} can use variable weights.

modified neglect of differential overlap

Semiempiric methods {modified neglect of differential overlap} (MNDO) can ignore overlap.

molecular modeling

Molecule-modeling programs {molecular modeling}, such as Alchemy III and SYBYL from Tripos, can use electrostatics or quantum mechanics.

non-linear partial least-squares

Non-parametric methods {non-linear partial least-squares, drug} (NPLS) can find least squares.

non-parametric method

Response-surface methods {non-parametric method}, such as ACE, NPLS, and MARS, can be non-parametric.

rule induction system

IF/THEN statement sets {rule induction system, drug} can make output from input.

score plot

Graphs {score plot} can plot compound activities.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Clustering

cluster analysis drug

In multidimensional property space, compound clusters make classes separated by distance {cluster analysis} (CA). CA reduces unimportant variables. Substructure, topological index, physico-chemical property, calculated physico-chemical property, or hydrophobicity can determine classes.

cluster significance

Using discrete or continuous data and embedded data can put compounds into groups by activity level {cluster significance analysis} (CSA). CSA locates small clusters in large spaces.

Cone and Hodgkin similarity index

Methods {Cone and Hodgkin similarity index} can measure molecular similarity.

discriminant-regression model

Models {discriminant-regression model} (DIREM) can locate small clusters in large spaces.

distance-b program

Methods {distance-b program} (EVE) can locate small clusters in large spaces.

hierarchical cluster

Unsupervised methods {hierarchical cluster analysis} (HCA) can measure distances between all points and make point vs. distance dendograms.

Jarvis-Patrick method

Structures can cluster in large databases by rating different compounds by similarity {Jarvis-Patrick method}.

k-nearest neighbor

Supervised methods {k-nearest neighbor} (k-NN) can calculate new-object distances from all other objects, to locate small clusters in large spaces.

partitioning

Processes {partitioning} can merge individuals into groups or split whole into clusters.

similarity measure

Values {similarity measure} can compare distances.

single class discrimination

Methods {single class discrimination} (SCD) can locate small clusters in large spaces.

supervised method

Classifications {supervised method} can use already known patterns and clusters.

trend vector analysis

Activity and descriptor correlation vectors {trend vector analysis} can rank compound similarity.

Ward clustering method

Hierarchical methods {Ward's clustering method} {Ward clustering method} can agglomerate compounds to find clustering.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Clustering-SIMCA

Soft Independent Modeling of Class Analogies

Supervised methods {Soft Independent Modeling of Class Analogies} (SIMCA) can use region-boundary or envelope models, to locate small clusters in large spaces.

class analogy

Clustering methods {class analogy} can be SIMCA methods.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Clustering-Distance

city-block distance

Distance measures {city-block distance} between structure-space points can be the same as Manhattan distance.

Manhattan distance

Distance measures {Manhattan distance} between structure-space points can be the same as city-block distance.

Minkowski distance

Distance measures {Minkowski distance} between structure-space points can be the same as Lp-metric.

Lp-metric

Distance measures {Lp-metric} between structure-space points can be the same as Minkowski distance.

Mahalanobis distance

Structure-space points have distances {Mahalanobis distance}.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Clustering-Linkage

centroid linkage

Hierarchical methods {centroid linkage} that agglomerate compounds can find clustering.

complete linkage

Hierarchical methods {complete linkage} that agglomerate compounds can find clustering.

single linkage

Hierarchical methods {single linkage} that agglomerate compounds can find clustering.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Factor Analysis

factor analysis

Processes have factors {factor analysis}. Physico-chemical or structural properties describe compounds and have components {descriptor, factor} {X-variable, factor} {X descriptor, factor}. Chemical activities relate to variables {response variable}.

canonical factor analysis

Methods {canonical factor analysis} can be for factor analysis.

centroid method

Methods {centroid method} can be for factor analysis.

combinatoric QSAR

QSAR {combinatoric QSAR} can find similarities using different descriptor combinations.

Comparative Molecular Moment Analysis

Moments of inertia, and dipole and quadrupole moments, can be descriptors to calculate molecular moments {Comparative Molecular Moment Analysis} (CoMMA). CoMMA depends on shapes and charges.

Correlation Analysis

Properties and structures have relations {Correlation Analysis}.

correspondence analysis

Factor-analysis methods {correspondence analysis} {correspondence factor analysis} (CFA) can use variable frequencies relative to activities, finds chi-square values, and finds principal components.

disjoint principal component

Principal components {disjoint principal component} (DPP) can be independent.

eigenvalue-one criterion

Thresholds {eigenvalue-one criterion} can be how many components have eigenvalues greater than one.

eigenvector projection

Unsupervised linear methods {eigenvector projection} can find factors.

Evolutionary Programming

Models {Evolutionary Programming} (EP) can add and subtract randomly selected variables, with crossing-over, and evaluate for "fitness" or best fit.

evolving factor analysis

Methods {evolving factor analysis} (EVA) can analyze ordered data.

explained variance percentage

Methods {percentage of explained variance} {explained variance percentage} can indicate number of components required to reach 90% of total variance.

extrathermodynamic approach

Parameters and descriptors can linearly relate to free energy {extrathermodynamic approach}.

free energy perturbation

Factor-analysis methods {free energy perturbation} (FEP) can use free-energy changes.

Free-Wilson approach

Binary descriptors can note molecule-substructure presence or absence {Free-Wilson approach}.

Genetic Function Algorithm

Linear property sets can have different values, change values by crossing-over between related such genes, and have random change {Genetic Function Algorithm} (GFA), to select best fit.

Hammett sigma value

Values {Hammett sigma value} can relate to electronic and electrostatic properties.

Hansch equation

Activity, partition coefficients for hydrophobicity, ionization degree, and molecular size relate {Hansch equation}.

latent variable

Variables {latent variable} can be linear-descriptor combination.

linear discriminant analysis

Supervised methods {linear discriminant analysis} (LDA), in which boundary surface minimizes region variance and maximizes variance between regions, can put compounds into groups by activity level.

linear free energy

log K = k1 * sigma + k2 {linear free energy equation, drug} (LFE).

linear learning machine

Supervised methods {linear learning machine} (LLM) can divide n-dimensional space into regions, using discriminant function.

maximum-likelihood method

Factor-analysis methods {maximum-likelihood method} can find factors.

multidimensional scaling

Metric or non-metric methods {multidimensional scaling} (MDS) can analyze similarity or dissimilarity matrices to find dimension number and place objects in proper relative positions.

multivariate adaptive regression spline

Non-parametric methods {multivariate adaptive regression spline} (MARS) can find factors.

Mutation and Selection Uncover Models

Models {Mutation and Selection Uncover Models} (MUSEUM) can add and subtract randomly selected variables, with no crossing-over, and evaluate for "fitness" or best fit.

non-linear iterative partial least-squares

Unsupervised linear methods {non-linear iterative partial least-squares} (NIPALS) can represent data as product of score matrix, for original observations, and loading-matrix transform, for original factors.

non-linear mapping

Topological mappings {non-linear mapping} (NLM) can be factor-analysis methods in which linear-variable combinations make two or three new variables.

predictive computational model

Information about compound physico-chemical properties can predict compound chemical or physiological behavior in vitro and in vivo {predictive computational model}.

principal component analysis

Variables {principal component} (PC) can be linear-descriptor combinations. Unsupervised linear method {principal component analysis, factor} (PCA) represents data as product of score matrix, for original observations, and loading-matrix transform, for original factors. PCA is factor-analysis method in which linear variable combinations make two or three new variables. PCA reduces unimportant variables.

principal component regression

Singular-value decomposition (SVD) can find best singular values for predicting {principal component regression} (PCR). SVD projects regression to latent structures.

principal factor analysis

Modified PCA {principal factor analysis} can find principal factors.

Procrustes analysis

Methods {Procrustes analysis} can identify descriptor sets for describing similarity.

QR algorithm

Methods {QR algorithm} can diagonalize matrices.

rank annihilation

Unsupervised linear methods {rank annihilation} can find factors.

Scree-plot

Residual variance approaches constancy {Scree-test, drug}, and plotted slope levels off {Scree-plot}, depending on component number.

singular value decomposition

In unsupervised linear methods {singular value decomposition, drug} (SVD), correlation matrix is product of score, eigenvalue, and loading matrices, with diagonalization using QR algorithm.

spectral mapping analysis

Factor-analysis methods {spectral mapping analysis} (SMA) can first take data logarithm to eliminate outliers and then subtract means from rows and columns, to leave only variation, showing which variables are important and how much.

structure space

Spaces {structure space} can have two or three principal components.

target-transformation

Methods {target-transformation factor analysis} can rotate features to match known pattern, such as hypothesis or signature.

Unsupervised Method

Factors and response variable have relations {Unsupervised Method}, without using factor information or predetermined models.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Factor Analysis-Design

factorial design

Designs {factorial design} can try to ensure design-space sampling, if position varies.

fractional factorial

Designs {fractional factorial design} can try to ensure design-space sampling, if position varies.

response surface method

Three-level designs {response surface method} (RSM) can have three factors that quantify relationships among responses and factors. RSM includes MLR, OLS, PCR, and PLS linear designs; non-linear regression analysis (NLR); and non-parametric methods, such as ACE, NPLS, and MARS.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Isomer Enumeration

Cayley tree structure

isomer-enumeration method {Cayley tree structure}.

CONGEN program

Isomer-enumeration methods {CONGEN program} can be successors to DENDRAL.

DENDRAL program

Isomer-enumeration methods {DENDRAL program} can be forerunners of CONGEN.

Henze and Blair recursion formulas

isomer-enumeration method {Henze and Blair recursion formulas}.

Polya enumeration theorem

Isomer-enumeration methods {Polya's enumeration theorem} {Polya enumeration theorem} can use group theory.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Molecular Orbital

molecular orbital

Electron orbitals {molecular orbital} can be for whole molecule.

ab initio analysis

Analyses {ab initio analysis} can use all electrons.

linear combinations of atomic orbitals

Adding atomic orbitals can approximate molecular orbitals {linear combinations of atomic orbitals} (LCAO).

perturbative configuration interaction

Semiempiric methods {perturbative configuration interaction using localized orbitals} (PCILO) can use perturbations.

semiempiric

Analyses {semiempiric} can use valence electrons and parameterize core electrons.

simple delta index

Sigma electrons can contribute {simple delta index, drug}.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Regression

regression for drugs

Factors, properties, or structures {regressor} can contribute to response values {regression, regressor} {Regression Analysis}.

canonical correlation

Regression can project to latent structures {canonical correlation} (CC), to put compounds in classes.

continuum regression

Regression {continuum regression} (CR) can project to latent structures, to put compounds in classes.

correlation matrix

Variance-covariance matrix {correlation matrix, drug} can scale to normalize data.

kernel algorithm

Regression can project to latent structures {kernel algorithm}, to put compounds in classes.

matrix diagonalization

Methods {matrix diagonalization, drug} can simplify data variance-covariance matrix.

non-linear regression

Parametric methods {non-linear regression} (NLR) can find descriptor coefficients by non-linear regression.

ridge regression

Regression can project to latent structures {ridge regression} (RR), to put compounds in classes.

Spearman rank correlation coefficient

Methods {Spearman rank correlation coefficient} can measure molecular similarity.

variance-covariance matrix

Complete, symmetric, square matrix {variance-covariance matrix} uses property values and structure values.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Regression-Least Squares

adaptive least-squares

Regression can project to latent structures {adaptive least-squares} {ALS algorithm}, to put compounds in classes.

classical least-squares

Methods {classical least-squares, drug} (CLS) can be the same as ordinary least-squares analysis.

Comparative Molecular Field Analysis

Partial least-squares {Comparative Molecular Field Analysis} (CoMFA) can analyze grid around site atom and find grid-point electrostatic and steric interactions, to make sampled-point descriptors.

fuzzy adaptive least

Compounds have different classes with different weights {fuzzy adaptive least-squares} (FALS).

Generating Optimal Linear PLS Estimations

Methods {Generating Optimal Linear PLS Estimations} (GOLPE) can use PLS and D-optimal design to select variables, and cross-validates.

inverse least-squares

Fitting methods {inverse least-squares} (ILS) can find regression line.

least-squares regression

Methods {least-squares regression, drug} can be the same as ordinary least-squares analysis.

linear least-squares

Methods {linear least-squares regression, drug} can be the same as ordinary least-squares analysis.

matrix bidiagonalization method

Partial least-squares methods {matrix bidiagonalization method, drug} can simplify data variance-covariance matrix.

multi-block PLS

Regression can project to latent structures {multi-block PLS}, to put compounds in classes.

multiple least-squares regression

Methods {multiple least-squares regression, drug} can be the same as ordinary least-squares analysis.

multiple linear regression

Methods {multiple linear regression} (MLR) can measure linear component dependence on physico-chemical or structural properties and finds descriptor coefficients.

multivariate least-squares regression

Methods {multivariate least-squares regression, drug} can be the same as ordinary least-squares analysis.

non-least-squares

Methods {non-least-squares} (NLS) can detect non-linear relationships.

ordinary least-squares

Fitting methods {ordinary least-squares} (OLS) can find descriptor coefficients.

partial least-squares

Methods {partial least-squares} (PLS) can use least-squares to find independent variables and dependencies among variables. It projects regression to latent structures. It maximizes latent-variable and observable covariation. It diagonalizes the matrix.

SAMPLS algorithm

Methods {SAMPLS algorithm} can apply PLS to trend vector analysis.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Statistical

best linear unbiased estimator

Estimates {best linear unbiased estimator} (BLUE) can give smallest variance among estimators.

standard error

Error measures {standard error} can be square root of MSE.

5-Chemistry-Biochemistry-Drug-Activity-Methods-Statistical-Squares

squares of differences

SSE, SSR, or SST {sum of squares of differences} {squares of differences sum}.

mean square error

SSE / (observation number + factor number - 1) {mean square error} (MSE).

SSE

Errors or residuals can cause sum {SSE} of squares of differences between observed and predicted responses.

SSR

Regression can cause sum {SSR} of squares of differences between observed and mean.

SST

Sum {SST} of squares of differences between predicted and mean makes total: SST = SSE + SSR.

5-Chemistry-Biochemistry-Drug-Experiment

drug experiment

Drugs have tests {drug experiment}.

experimental design

Samples can test properties and activities. Experiment uses numbers and sample types from population, as well as methods and instruments. Three-level design assigns three levels (-1,0,1) to each factor to determine how responses vary with factors or variables, for making mechanistic physico-chemical models, using physical chemical properties as factors, or empirical polynomial models, using arbitrary variables as factors. Three-level mixture design determines whether factor is useful or significant or not. Two-level design assigns two levels (0,1) to each factor to determine whether factor is useful or significant, for screening, searching, or filtering.

kinetics

Experiments can read samples multiple times over time to find reaction rate or inhibition constant.

assay experiment

Biological reaction series can makes protocols {assay, experiment}. Protocol or method series use reagents to identify compounds, genes, proteins, or quantities.

protocol for experiment

Methods {protocol, experiment}| can run experiments. Experiments can perform steps or tasks on samples: prepare samples, mix with reagents, hybridize, wash, detect, and analyze.

replication in experiment

Samples can be read more than once {replication, sample}.

scoring

In screening, calculated results translate into given ranges {scoring}, like high, medium, or low.

5-Chemistry-Biochemistry-Drug-Experiment-Design

Box-Behnken design

three-level design {Box-Behnken design}.

CARSO approach

Experimental designs {CARSO approach} can be for random compound screening in experiment series.

central composite design

three-level design {central composite design}.

Craig plot

Experimental designs {Craig plot} can be for random compound screening in experiment series.

D-optimal design

Test-set selection methods {D-optimal design} can try to ensure design-space sampling, if positions vary, and can account for excluded volumes.

sequential optimization

Experiment designs {sequential optimization} can use steps toward optimum.

Topliss tree

Experimental designs {Topliss tree} can be for random compound screening in experiment series.

5-Chemistry-Biochemistry-Drug-Experiment-Kinds

dose response curve

Experiments {dose response curve} can read samples at different concentrations and fit IC50 curves.

ELISA

Experiments {ELISA} can back-calculate sample concentration, using reference curve.

High-Throughput Screening

Automated assays {High-Throughput Screening} (HTS) can test many diverse compounds against enzymes or cell targets, to identify possible new drugs.

pooling

More than one sample can be in wells {pooling} in screening experiment. Samples mix in plate wells according to patterns, so system measures all samples the same number of times. Total well number is fewer than with one sample per well.

ratio experiment

Experiments {ratio experiment} can read samples twice, for agonist vs. antagonist, to determine activity ratios.

screening for drug

Automated assays {screening} {high-throughput screening} can identify promising compounds from compound libraries.

users and groups

Roles (types of users) have a set of privileges. Users have roles.

inventory

Inventory database has sample IDs.

experiment type: ELISA

Plate has high and low controls (averages), dose-response titration (IC50), and replicated samples (averages of % inhibition); Fit the result into the standard curve for a first estimate IC50, and back calculate the concentration of an expressed protein by using a standard reference curve on each plate. Look for the well that has a result which falls on the linear portion of the standard curve.

experiment type: ratio

Each plate is read twice, first reading the growth of a specific protein, and second measuring the survival of various cells (or agonist vs. antagonist receptors). % inhibitions are calculated for each of these readings, and then the ratio. Sort on any of the three results. Since plates are carried from one reader station to the next, they may get out of order, may be put into the reader backwards, or may get dropped, so data system should be able to deal with all of these problems. This is a case of 'multiple data points per well'.

experiment type: dose response, multiple calculations

Several different models calculate, fit, and display the IC50 curves simultaneously, like straight line regression and 4-parameter curve fitting, with constant high and low inflection points. Then register one or more, with model name, parameters, and comments.

experiment type: titration

From each daughter plate, 3 to 4 assay plates at different concentrations are made. An activity value is calculated for each well, as well as the activity changes as a function of concentration.

experiment type: titration and dose response across plates

A single 96 well plate is filled with 48 samples in duplicate. The plate is then copied across 8 other plates at different concentrations. The result from the 9 plates is used to calculate a dose response curve and IC50.

experiment type: no controls on data plates

All controls (high, low, reference, dose-response curve) are on one or more reference plates, interspersed throughout the runset. Calculate a 'curve' for the standards on the reference plates, by plate sequence or time. Could use controls only on nearest reference plate.

experiment type: whole plant experiment

Growth of different plant species at time intervals, with qualitative and quantitative (Scores) results. At the end of the experiment, a report of the changes over time. A ''score' is based on observing the well and is a coded value that means something like 'severe yellowing of stem' or "intense chlorosis of stem" with more than one score per well.

experiment type: colormetric assay

Inhibition makes well white, but experiment failure makes "milky white". A scientist can see the difference, but the automated reader can be fooled. so scientist marks specific wells as bogus BEFORE the results are read into the data system.

experiment type: kinetics

Each well is read multiple times over time and the calculated value is based on the multiple raw values. All raw data is saved or only the final derived value. Plot of the timed values.

experiment type: Ki values

Dose response experiment, with a ligand of known activity value and concentration recorded. The IC50, and further calculations based on IC50, ligand activity, and ligand concentration are saved for each sample.

experiment type: pooling and replicates

Pooled plates have replicated mixtures. Same as HTS and REP, but with a reference to mixture in Inventory.

experiment type: non-plate based experiments

Row of tubes, lawn format, and so on.

variable group

A candidate variable group is selected or built. The group should take account of the dimension variables to be used for the RFM upload and for the layout. The group should take account of the layout actual and placeholder values. The group should have clauclations from raw data and places to mark data invalid or promotable. The group might have a Review check.

layout

A candidate layout for the Well table is developed. The layout should have an actual concentration, actual well types for High/Low/Data/Reference wells, and placeholders for the sample IDs. The dimension, calculation, and set variables should work with the layout.

calculations

Candidate calculations are selected or made for the calculation variables of the variable group. The calculations need to follow the default or nondefault rules for calcs, especially for parent-child relations, performance, and using ASSOC, MATCHALL, and CONDITION= correctly.

reader file and format

An actual or realistic reader file is available from such an experiment, and the reader file sections are made and tested, and the sections assigned to variables of the variable group. Ordinals are assigned to Row and Column variables, along with dimensions that match the variable group and layout.

protocols and templates

Protocol assays or attributes might be added to the protocol. (Sections or templates might be built for the protocol display.) A protocol is selected or made, which contains the variable group, layout(s), and RFM formats, plus any required fields.

dictionaries and terms

Dictionary terms and dictionaries might be added for use in the protocol.

result tables

Result tables are selected or made, together with the result maps from the variable group to the result table(s).

experiments

The completed protocol is used to start an experiment, the layout and the RFM format are added, then the reader file(s) are selected. Any placeholders in the layout must be filled in. (Assembler). The experiment is calculated and stored.

analysis

The experiment is analyzed to determine if any data is invalid or questionable, and a recalculation and store occurs. A rule might be used for automatic checking for bad controls, dropped plates, and so on. The analysis might include a mod to a calc formula, data, or a change of model for a curve.

decision

The experiment is analyzed to determine if any samples are worthy of further experimentation. Such samples are marked for further testing. A score might be assigned based on rules.

review and/or release

A review is made (typically by a higher authority) of the results. That such a review has been made is noted somewhere. Perhaps the data is allowed to be used or seen by other workgroups, or is sent to corporate database.

browsing

Other persons at a company want to see a summary of the validated results, in a set format for all researchers, to avoid duplication and error.

5-Chemistry-Biochemistry-Drug-Mechanics

bioavailability

Blood drug amount {bioavailability} relates to dose.

Blood-Brain Barrier penetration

Brain-compartment drug concentration to blood-compartment drug concentration makes ratios {Blood-Brain Barrier penetration}.

diffusivity of drug

Drug diffusion calculations {diffusivity} can measure drug-diffusion ease.

disposition of drug

Distribution and elimination can combine {disposition, drug}.

distribution of drug

Drugs have different concentrations in various body tissues {distribution, drug}.

elimination of drug

Excretion {elimination, drug} uses urine and feces.

enterocyte

Ingested drugs affect intestinal-wall cells {enterocyte}.

enterohepatic cycling

Bile goes back to GI tract for recycling {enterohepatic cycling} (EHC).

intrinsic clearance

Liver removes drugs from blood {intrinsic clearance} (CL).

molecular weight theory

Compounds above 500 to 700 cannot diffuse across lipid membrane {molecular weight theory}.

oral bioavailability

Percentage of orally administered drug in general blood circulation, or in urinary excretion, compares to intravenous administration {absolute oral bioavailability} {oral bioavailability}.

portal vein

A vein {portal vein} carries blood to liver from GI tract.

5-Chemistry-Biochemistry-Drug-Mechanics-Absorption

absorption of drug

Active or passive transport carries drug from intestine to portal vein {absorption, drug}.

human intestinal absorption

Compounds absorbed from intestine {human intestinal absorption} (HIA) go to portal vein.

motility intestine

Intestines have contents travel rate {motility}.

pH partition theory

Acidic or neutral drugs can diffuse across GI-tract lipid membrane, but basic drugs cannot diffuse {pH partition theory}.

predicted fraction

Drug goes from intestine to portal vein {predicted fraction of human absorption} (Fa). Fraction is in percent.

5-Chemistry-Biochemistry-Drug-Mechanics-Lipophilicity

lipophilicity

Compounds can have good solubility in lipids {lipophilicity}.

Fujita-Hansch pi value

Values {Fujita-Hansch pi value} can relate to lipophilicity.

log P

Octanol/water partition coefficient logarithms {log P} can measure lipophilicity.

molecular lipophilicity potential

Hydrophobicity measures {molecular lipophilicity potential} (MLP) can calculate lipophilicity surface.

octanol-buffer partition

Lipophilic compounds can diffuse across lipid membrane {octanol-buffer partition coefficient theory}.

P-glycoprotein

On brain-capillary endothelial-cell insides, proteins {P-glycoprotein} can prevent high-lipophilicity drugs from crossing BBB.

5-Chemistry-Biochemistry-Drug-Mechanics-Transport

transport of drug

Drugs must get to sites {transport, drug} {drug transport}.

passive transport of drug

Diffusion carries molecules across membranes {passive transport}.

5-Chemistry-Biochemistry-Drug-Metabolism

drug metabolism

Drug breakdown by oxidation {drug metabolism} is mainly in liver.

adduct

Compounds can have an added group {adduct}.

drug-drug interaction

Drug can inhibit or induce another drug {drug-drug interaction}.

flavoprotein

Proteins {flavoprotein} can bind FAD or FMN.

glutathione

Molecules {glutathione} (GSH) can participate in phase II conjugations.

hepatic first-pass elimination

Phase I oxidations, Phase II conjugations, and transport into bile reduce drug in hepatic blood {hepatic first-pass elimination} (HFPE).

iron-oxene

Iron compounds {iron-oxene} {iron-oxenoid} can contain free oxygen atoms.

metabolite

Drug metabolism makes products {metabolite}.

metabolite intermediate complexation

Nitrosoalkanes irreversibly bind to reduced heme intermediates of CYP450 enzymes {metabolite intermediate complexation}.

mutagenicity

Compounds or forces can mutate genes {mutagenicity}.

regioselectivity

Metabolism percentage {regioselectivity} categorizes sites as major, minor, or unobservable. Rate constant differences among sites cause metabolic-site regioselectivity.

selectivity of drug

Drugs can affect targets {selectivity, drug} and other sites.

5-Chemistry-Biochemistry-Drug-Metabolism-Binding

agonist molecule

Substrates {agonist} can bind to receptors and cause biologic response.

antagonist molecule

Substrates {antagonist, chemistry} can bind to receptor but cause no biologic response.

5-Chemistry-Biochemistry-Drug-Metabolism-Chemical Reaction

acetylation

Hydrogen atoms can bind to carbon atoms {acetylation}.

amino acid conjugation

Amino acids can bind to carboxylic-acid groups {amino acid conjugation}, on anti-inflammatory, hypolipidaemic, diuretic, and analgesic drugs.

bioactivation

Enzymes can change drugs to make them toxic {bioactivation}.

biotransformation

Drug metabolism has oxidations and reductions {biotransformation}.

charge-transfer coupling

Two charges can exchange {charge-transfer coupling} in reactions.

conjugation of molecule

Molecules can attach small molecule {conjugation, molecule}.

cyclization

Processes can make rings {cyclization}.

glucuronic acid conjugation

Glucuronic acid allows glucuronide formation {glucuronic acid conjugation}.

glutathione conjugation

Molecules can conjugate with glutathione {glutathione conjugation} to form mercapturic acid.

hydrogen bond acceptor

Atoms {hydrogen bond acceptor} (HBA) can add hydrogen atom.

hydrogen bond donor

Atoms {hydrogen bond donor} (HBD) can release hydrogen atom.

hydrogen transfer

Hydrogen atoms can abstract {hydrogen transfer}.

hydroxylation

Hydrogen atoms can bind to oxygen atom {hydroxylation}.

induced fit

Enzymes can change conformation to allow substrate binding {induced fit}.

intrinsic activity

Drugs can form complexes with receptors and then cause chemical or conformational changes {intrinsic activity, drug}.

Phase I enzyme reaction

Drug metabolism has oxidation or reduction {Phase I enzyme reaction}.

Phase II enzyme reaction

Drug metabolism has conjugation with small molecules {Phase II enzyme reaction}.

proton abstraction

Hydrogen atoms removed from molecules {proton abstraction} can make water.

sulfate conjugation

After ATP activates sulfate, sulfotransferase makes sulfate esters {sulfate conjugation}.

5-Chemistry-Biochemistry-Drug-Metabolism-Energy

guanidine diphosphate

nucleophosphate energy compound {guanidine diphosphate} (GDP).

uridine diphosphate

Energy molecules {uridine diphosphate} (UDP) can participate in phase II reactions.

5-Chemistry-Biochemistry-Drug-Metabolism-Enzyme

adenylate cyclase

Enzymes {adenylate cyclase} {adenylcyclase} can alter cAMP.

carboxylesterase

Enzymes {carboxylesterase} can catalyze phase I reactions.

cytochrome P-450

Enzymes {cytochrome P-450} catalyze phase I reactions 3A4, 2D6, 2C9, 1A2, and 2E1.

epoxide hydratase

Enzymes {epoxide hydratase} {epoxide hydrolase} can oxidize olefins and aromatics to make epoxide or oxirane metabolites. It can produce carcinogens.

glucuronyl-transferase

Enzymes {glucuronyl-transferase} can catalyze phase II reactions, adding glucuronide to drugs.

glutathione-S-transferase

Enzymes {glutathione-S-transferase}, in liver-cell cytoplasm, can catalyze phase II reactions to conjugate compounds to glutathione.

microsomal flavoprotein mono-oxygenase

Enzymes {microsomal flavoprotein mono-oxygenase} can oxidize nitrogen or sulfur organics.

microsomal hydroxylase

Enzymes {microsomal hydroxylase} can catabolize many compounds, mostly by oxidation, in endoplasmic reticulum.

mixed-function oxidase

Enzymes {mixed-function oxidase} (MFO) can catabolize many compounds, mostly by oxidation, in endoplasmic reticulum.

phospholipase A2

Enzymes {phospholipase A2} can catabolize lipids.

phospholipase C

Enzymes {phospholipase C} can catabolize lipids.

protein kinase

Enzymes {protein kinase} can catabolize proteins.

uridine diphosphoglucose

Enzymes {uridine diphosphoglucose transferase} {uridine-diphosphate-glucuronosyl-transferase} (UDP-GT) (UGT) can catalyze phase II reactions, adding glucuronide to drugs.

5-Chemistry-Biochemistry-Drug-Metabolism-Inhibition

drug inhibition

Chemicals can inhibit drugs {drug inhibition}. Inhibitor has binding constant.

allosteric non-competitive inhibition

Inhibitor can bind to non-active site {allosteric non-competitive inhibition}.

entry inhibitor

Drugs {entry inhibitor} can prevent viruses from entering cells.

integrase inhibitor

Drugs {integrase inhibitor} can prevent virus DNA from inserting into host DNA.

maturation inhibitor

Drugs {maturation inhibitor} can block gag-protein protease receptor, so gag protein is not split, and HIV virus coat is not made. PA-457 comes from betulinic acid from Taiwan herb, plane trees, and birch trees.

mechanism-based inhibition

Metabolized compounds can bind to enzymes {mechanism-based inhibition}.

protease inhibitor

Drugs {protease inhibitor} can inhibit protease enzymes.

5-Chemistry-Biochemistry-Drug-Metabolism-Orbital

highest occupied molecular orbital

Most-reactive electron {highest occupied molecular orbital} (HOMO) can be in electron-rich nucleophilic molecules.

lowest unoccupied molecular orbital

Most-reactive electron {lowest unoccupied molecular orbital} (LUMO) can be in electron-poor electrophilic molecules.

5-Chemistry-Biochemistry-Drug-Metabolism-Rate

absolute metabolism rate

Total metabolism has rate {absolute metabolism rate}.

enzyme kinetics

Reaction rate typically depends on concentration and temperature {enzyme kinetics}.

lability

Metabolism rate at site has estimated ease {lability}.

Michaelis-Menten constant

Enzymes have binding constants {Michaelis-Menten constant} (Km).

5-Chemistry-Biochemistry-Drug-Metabolism-Site

labile site

Sites {labile site} can have high metabolism rate and low activation energy.

moderate site

Sites {moderate site} can have intermediate metabolism rate and activation energy.

stable site

Sites {stable site} can have low metabolism rate and high activation energy.

5-Chemistry-Biochemistry-Drug-Selection

asymmetric set of drug

Active compounds have small clusters {asymmetric set} in compound space.

biological screening

Automated assays {biological screening} can identify promising compounds from compound libraries.

embedded set of drug

Active compounds have small clusters {embedded set} in compound space.

inventory of samples

Sample collections {inventory, sample} {sample inventory} can be ready for testing, stored in plate wells.

lead finding

From many compounds, processes {lead finding} {lead generation} {lead selection} can identify compounds that have significant chemical activity.

lead optimization

Processes {lead optimization} can efficiently identify structure-activity relationships for generated leads.

outlier

Sample points {outlier} can be far from expected values.

promotion of sample

Samples can go to further testing {promotion}.

5-Chemistry-Biochemistry-Drug-Structure

drug structure

Drug-receptor geometry {drug structure} is a physico-chemical property and can be quantitative.

structure-activity relationships

Drugs have structure-activity relationships (SAR), which can be quantitative (QSAR). Drugs have property-activity relationships.

activity

Drug activity equals physicochemical-variable function. Drug activity relates to concentration, partition coefficient, or product formation. Stages have probabilities. Drug activity is proportional to concentration product, complexing probability, changing probability, and partitioning probability.

activity: complex formation

Drugs form complexes with receptors {intrinsic activity, complex}. Drugs {chemotherapeutic drug} can cause chemical reactions or conformational changes. Drugs {pharmacodynamic drug, complexes} can make complexes but do not change conformation or cause reactions.

Complex-formation probability is formation-reaction equilibrium constant. Equilibrium constant depends on both equilibrium type and substituent electronic influence on reaction center. log(K) = k1 * sigma + k2 {linear free energy equation, structure} (LFE). log(1 / concentration) = k1 * sigma + k2. Electronic influences are universal and have tables of values. Equilibrium type results from multiple regression analysis of simultaneous equations.

activity: partitioning

If hydrophobicity affects drug structure, partition coefficient affects activity. log(K) = k3 * pi + k1 * sigma + k2 and log(1 / concentration) = k3 * pi + k1 * sigma + k2. Partition coefficients are universal and have tables of values.

activity: transport

Drugs have to get to target site. Drug transport involves diffusion, active transport, adsorption, binding to serum proteins, or membrane interactions. Mechanisms that oppose drug transport are excretion, metabolism, and localization in fat. Excretion is faster for hydrophilic. Metabolism is faster for hydrophobic. Localization in fat is faster for hydrophobic. Drug transport affects drug activity. log(K) = k3 * pi + k1 * sigma + k2 - k4 * pi^2. log(1 / concentration) = k3 * pi + k1 * sigma + k2 - k4 * pi^2. Drug transport factors are universal and have tables of values.

structure

Molecule structure depends on atom types, atom numbers, chemical bonds, spatial relations, and atom locations. Features are either present or absent, with no interactions.

structure: molecular connectivity indices

Kier and Hall used features such as electrotopologic state index, valence, molecular shape and flexibility {kappa index, structure}, branching, unsaturation, cyclization, and heteroatom position. They found molecular connectivity indices, based on Randic's branching index, calculated from hydrogen-suppressed chemical graph or skeleton structure. For example, atoms can have number of sigma electrons contributed {simple delta index, structure} or number of valence electrons {valence delta}.

structure: molecular orbital

Quantum-mechanical structure description uses molecular orbital (MO) theory. Molecular orbitals depend on electron location and energy. Total conformation energy gives probability. MO typically ignores solvents.

Highest occupied molecular orbital gives the most-reactive electron for electron-rich nucleophilic molecules. Lowest unoccupied molecular orbital gives the most-reactive electron for electron-poor electrophilic molecules.

MO can test reaction paths and find thermodynamic information, by checking energies in different configurations.

Molecular orbitals can be linear combinations of atomic orbitals (LCAO). Atomic-orbital contribution probability is linear-coefficient squared, and point charge is probability sum.

structure: interactions

Comparative Molecular Field Analysis (CoMFA) uses partial least-squares to analyze grid around site atom and find grid-point hydrophobic, electrostatic, and steric interactions.

structure: ab initio

Ab initio analysis uses electron locations to find charges, electrostatic potentials, dipole moments, ionization energies, electron affinity, and activation energies. Semiempiric analysis uses only valence electrons and parameterizes core electrons. Modified neglect of differential overlap (MNDO) ignores overlaps. Perturbative configuration interaction using localized orbitals (PCILO) uses perturbations. Varying bond angles, bond lengths, and torsion angles can find minimum energy and preferred conformation.

structure: axial-equatorial configuration

Non-conjugated-ring substituent positions can be in ring plane {equatorial configuration} or perpendicular {axial configuration}.

structure: branching

Carbon chain can have fork {branching}.

structure: ionization degree

Molecule can have charge {degree of ionization} {ionization degree}.

structure: dipole moment

Opposite charges can separate by distance.

structure: electrostatic potential

Electric potential energy comes from electric field.

structure: molecular similarity

Molecules can be similar in 3D atomic configuration, atom pairs, chemical graphs, electron densities, field potentials, molecular fragments, molecular properties, molecular surfaces, steric volumes, or topological/information theory indexes.

structure: orientation

Molecule spatial alignment is at receptor site.

structure: radical

Atoms can have one electron in outer orbital.

structure: singlet or triplet state

Orbital state can have paired electrons {singlet state}. Orbital state can have unpaired electrons {triplet state}.

Chemical Abstracts Service

Connection tables number non-hydrogen atoms, name atomic elements, name atom number to which they connect, and name atom types {Chemical Abstracts Service} (CAS).

Chemical Descriptor Space

Molecules can be vectors, including chemical activity, in abstract space {Chemical Descriptor Space} (CDS).

combinatorial chemistry

Base compounds {building block} can attach one to four small molecules {combinatorial chemistry} to add functional groups and make compound libraries with molecular weights 300 to 750.

connection table

Tables {connection table} can describe three-dimensional structures.

connectivity matrix

Matrices {connectivity matrix} can graph molecular connections.

Coulombic potential

Electrostatic fields make potentials {Coulombic potential}.

desolvation

Polar solute can cross lipid membrane if hydrogen bonds to water break {desolvation}. Polar solute with fewer hydrogen bonds to water and lower hydrogen-bonding potentials can diffuse more easily.

electrotopologic state index

Indexes {electrotopologic state index} can depend on topology structures.

encoding tag

Molecular markers {encoding tag} can track combinatorial-chemistry molecules.

hetero

Molecule atoms {hetero} can be not carbon C or hydrogen H. Hetero can refer to solvent, non-solvent, water, ion, or ligand atoms.

heterocyclic compound

Compounds {heterocyclic compound} can have rings with atoms other than carbon.

hydrophobicity

Molecular regions can repel water {hydrophobicity}.

isoform

Cytochrome P450 has types {isoform}.

library of compounds

Combinatorial chemistry makes compound permutations {library of compounds}.

nearest neighbor table

Tables {nearest neighbor table} can rank different compounds by similarity.

pharmacophore

Superimposed molecules show constants across diverse molecules and so identify sites and reactions {pharmacophore}.

similarity matrix

Molecules have atomic properties, functional groups, and molecular properties {similarity matrix}.

superoxide anion

Oxygen can have positive charge {superoxide anion}.

virtual compound library

Possible compound permutations can be in database {virtual compound library}.

Wiswesser line notation

Strings {Wiswesser line notation} (WLN) can uniquely describe three-dimensional structure.

X-ray structure

X-ray crystallography patterns {X-ray structure} can indicate atom positions.

5-Chemistry-Biochemistry-Drug-Validation

validation methods

Methods {validation methods} can check structure-activity relationship correlations, predictions, and designs.

bootstrapping validation

Validation methods {bootstrapping validation method} can use only internal data.

cross-validated correlation

Methods {cross-validated correlation coefficient} can validate and predict data.

cross-validation

For all data subsets, algorithms {cross-validation} (CV) can remove one data subset and calculate remainder.

external validation

Other data can pair with model to predict activity {external validation}.

Fisher F-test

Validation methods {Fisher F-test} can use F test.

fitness function

Validation methods {fitness function} (FIT) can measure fit.

jackknife validation

cross-validation method {jackknife validation method, drug}.

lack-of-fit

Methods {lack-of-fit} (LOF) can measure fit.

leave-groups-out

cross-validation method {leave-groups-out, drug} (LGO).

leave-one-out

cross-validation method {leave-one-out, drug} (LOO).

predictive residual sum of squares

Methods {predictive residual sum of squares, drug} (PRESS) can measure fit.

scrambling dependent Y-values

cross-validation method {scrambling dependent Y-values, drug}.

standard deviation method

Methods {standard deviation method, drug} (sPRESS) can measure fit.

standard error of predictions

Methods {standard error of predictions, drug} (SDEP) can measure fit.

standard error of regression

Methods {standard error of regression, drug} can measure fit.

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5-Chemistry-Biochemistry

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Date Modified: 2022.0225