Epigallocatechin

Identification

Name
Epigallocatechin
Accession Number
DB03823  (EXPT01331)
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • (-)-epi-gallocatechin
  • (-)-epigallocatechin
  • (-)-epigallocatechol
  • (−)-epigallocatechin
  • 3,3',4',5,5',7-flavanhexol
  • Antiscurvy factor C2
  • EGC
  • Epi-gallocatechin
  • Galloepicatechin
  • L-epigallocatechin
External IDs
NSC-674039
Categories
UNII
7Z197MG6QL
CAS number
970-74-1
Weight
Average: 306.2675
Monoisotopic: 306.073952802
Chemical Formula
C15H14O7
InChI Key
XMOCLSLCDHWDHP-IUODEOHRSA-N
InChI
InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1
IUPAC Name
(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
SMILES
O[[email protected]@H]1CC2=C(O[[email protected]@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

David Burdick, Heinz Egger, Andrew Gum, Ingo Koschinski, Elena Muelchi, Isabelle Prevot-Halter, "Process for the production of (-)-epigallocatechin gallate." U.S. Patent US20060069046, issued March 30, 2006.

US20060069046
General References
Not Available
External Links
Human Metabolome Database
HMDB38361
KEGG Compound
C12136
PubChem Compound
72277
PubChem Substance
46506265
ChemSpider
65231
BindingDB
50187665
ChEBI
42255
ChEMBL
CHEMBL47386
HET
EGT
PDB Entries
1jnq

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentProstate Cancer1

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 Solubility0.871 mg/mLALOGPS
logP0.71ALOGPS
logP1.49ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.73ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area130.61 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.98 m3·mol-1ChemAxon
Polarizability29.14 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9654
Blood Brain Barrier-0.5331
Caco-2 permeable-0.8956
P-glycoprotein substrateSubstrate0.5972
P-glycoprotein inhibitor INon-inhibitor0.8953
P-glycoprotein inhibitor IINon-inhibitor0.9734
Renal organic cation transporterNon-inhibitor0.9458
CYP450 2C9 substrateNon-substrate0.8227
CYP450 2D6 substrateNon-substrate0.8771
CYP450 3A4 substrateNon-substrate0.6345
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9041
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.817
Ames testNon AMES toxic0.7658
CarcinogenicityNon-carcinogens0.9539
BiodegradationNot ready biodegradable0.7895
Rat acute toxicity1.8700 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9666
hERG inhibition (predictor II)Non-inhibitor0.7487
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0978700000-567c7251027c80e91a01
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0967700000-febb7658ba2d5bd6d9b6
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
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0529000000-0036b0386a7ade78fcac
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00vi-0690000000-702c5a1e065692895b3a
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00vi-0690000000-7844ed1a917693a67b37
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-002r-0910000000-8dfe0ba4e2ec1225213f
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00p0-0951000000-95142c4b42b35c4bdac9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-c79003b472daf421e492
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0910000000-f92cf1606a46a5b16f4f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0910000000-2026f33ac95d368b5268

Taxonomy

Description
This compound belongs to the class of organic compounds known as epigallocatechins. These are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavans
Direct Parent
Epigallocatechins
Alternative Parents
7-hydroxyflavonoids / 5-hydroxyflavonoids / 4'-hydroxyflavonoids / 3-hydroxyflavonoids / 3'-hydroxyflavonoids / 1-benzopyrans / Pyrogallols and derivatives / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids
show 5 more
Substituents
Epigallocatechin / 3'-hydroxyflavonoid / 3-hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Hydroxyflavonoid / 1-benzopyran / Chromane / Benzopyran
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
catechin, flavan-3,3',4',5,5',7-hexol (CHEBI:42255) / Flavans, Flavanols and Leucoanthocyanidins, Flavan 3-ols (C12136) / Flavans, Flavanols and Leucoanthocyanidins (LMPK12020004)

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:33