2-DEOXY-3,4-BIS-O-[3-(4-HYDROXYPHENYL)PROPANOYL]-L-THREO-PENTARIC ACID

Identification

Generic Name
2-DEOXY-3,4-BIS-O-[3-(4-HYDROXYPHENYL)PROPANOYL]-L-THREO-PENTARIC ACID
DrugBank Accession Number
DB08322
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 456.3989
Monoisotopic: 456.10564686
Chemical Formula
C23H20O10
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlycogen phosphorylase, muscle formNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamic acids and derivatives
Sub Class
Hydroxycinnamic acids and derivatives
Direct Parent
Coumaric acid esters
Alternative Parents
Tetracarboxylic acids and derivatives / Coumaric acids and derivatives / Cinnamic acid esters / Styrenes / Fatty acid esters / 1-hydroxy-2-unsubstituted benzenoids / Monosaccharides / Enoate esters / Carboxylic acids / Organic oxides
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Substituents
1-hydroxy-2-unsubstituted benzenoid / Alpha,beta-unsaturated carboxylic ester / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Cinnamic acid ester / Coumaric acid ester
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
66G69TD43K
CAS number
Not Available
InChI Key
VJLMRHSHSNLOGC-NOPZTHQXSA-N
InChI
InChI=1S/C23H20O10/c24-16-7-1-14(2-8-16)5-11-20(28)32-18(13-19(26)27)22(23(30)31)33-21(29)12-6-15-3-9-17(25)10-4-15/h1-12,18,22,24-25H,13H2,(H,26,27)(H,30,31)/b11-5+,12-6+/t18-,22+/m0/s1
IUPAC Name
(2R,3S)-2,3-bis({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy})pentanedioic acid
SMILES
[H][C@@](CC(O)=O)(OC(=O)\C=C\C1=CC=C(O)C=C1)[C@@]([H])(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O

References

General References
Not Available
PubChem Compound
11669698
PubChem Substance
99444793
ChemSpider
9844429
BindingDB
50430005
ChEMBL
CHEMBL1234956
ZINC
ZINC000013339564
PDBe Ligand
OFF
PDB Entries
2off

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0287 mg/mLALOGPS
logP3.54ALOGPS
logP3.72ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area167.66 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity113.93 m3·mol-1ChemAxon
Polarizability44.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8679
Blood Brain Barrier+0.8035
Caco-2 permeable-0.7036
P-glycoprotein substrateSubstrate0.5134
P-glycoprotein inhibitor INon-inhibitor0.7871
P-glycoprotein inhibitor IINon-inhibitor0.5668
Renal organic cation transporterNon-inhibitor0.8836
CYP450 2C9 substrateNon-substrate0.766
CYP450 2D6 substrateNon-substrate0.9085
CYP450 3A4 substrateNon-substrate0.6324
CYP450 1A2 substrateNon-inhibitor0.8552
CYP450 2C9 inhibitorNon-inhibitor0.8354
CYP450 2D6 inhibitorNon-inhibitor0.8696
CYP450 2C19 inhibitorNon-inhibitor0.8651
CYP450 3A4 inhibitorNon-inhibitor0.7806
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7806
Ames testNon AMES toxic0.8327
CarcinogenicityNon-carcinogens0.884
BiodegradationNot ready biodegradable0.7486
Rat acute toxicity2.7184 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9618
hERG inhibition (predictor II)Non-inhibitor0.9226
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:30 / Updated at June 12, 2020 16:52