Identification
NameEpigallocatechin
Accession NumberDB03823  (EXPT01331)
TypeSmall Molecule
GroupsExperimental
DescriptionNot 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
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII7Z197MG6QL
CAS number970-74-1
WeightAverage: 306.2675
Monoisotopic: 306.073952802
Chemical FormulaC15H14O7
InChI KeyXMOCLSLCDHWDHP-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[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentMalignant Neoplasm of Prostate1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.871 mg/mLALOGPS
logP0.71ALOGPS
logP1.49ChemAxon
logS-2.5ALOGPS
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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0529000000-0036b0386a7ade78fcacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0690000000-702c5a1e065692895b3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0690000000-7844ed1a917693a67b37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-002r-0910000000-8dfe0ba4e2ec1225213fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-002r-0910000000-8dfe0ba4e2ec1225213fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00p0-0951000000-95142c4b42b35c4bdac9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00p0-0951000000-95142c4b42b35c4bdac9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c79003b472daf421e492View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-f92cf1606a46a5b16f4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-2026f33ac95d368b5268View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentEpigallocatechins
Alternative Parents7-hydroxyflavonoids / 5-hydroxyflavonoids / 4'-hydroxyflavonoids / 3-hydroxyflavonoids / 3'-hydroxyflavonoids / 1-benzopyrans / Pyrogallols and derivatives / Resorcinols / Catechols / Alkyl aryl ethers
SubstituentsEpigallocatechin / Hydroxyflavonoid / 7-hydroxyflavonoid / 5-hydroxyflavonoid / 4'-hydroxyflavonoid / 3-hydroxyflavonoid / 3'-hydroxyflavonoid / 1-benzopyran / Benzopyran / Chromane
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorscatechin, 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 June 11, 2017 16:25