Epigallocatechin (YMDB01682)

Identification

YMDB ID

YMDB01682

Name

Epigallocatechin

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

(-)-Epigallocatechin, also known as epigallocatechol, belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins 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. Based on a literature review a significant number of articles have been published on (-)-Epigallocatechin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(-)-3,3',4',5,5',7-Flavanhexol
(-)-Epigallocatechin
Epigallocatechin 3-gallate
Epigallocatechol
L-Epigallocatechin
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
2,3-cis-Epigallocatechin
(-)-cis-3,3',4',5,5',7-Hexahydroxyflavan
(-)-cis-3,3',4',5,5',7-Hexahydroxyflavane
(-)-Epigallocatechol
Antiscurvy factor C2
EGC
Epigallocatechin
l-Epigallocatechol
Gallocatechol, (2R-trans)-isomer
Gallocatechol
Gallocatechol, (2R-cis)-isomer
Gallocatechin
(-)-3,3’,4’,5,5’,7-Flavanhexol
(-)-epi-Gallocatechin
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-trihydroxychroman
(2R,3R)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
1-epi-3',4',5',5,7-Pentahydroxy-3-flavanol
1-epi-3’,4’,5’,5,7-Pentahydroxy-3-flavanol
3,3',4',5,5',7-Flavanhexol
3,3’,4’,5,5’,7-Flavanhexol
Galloepicatechin
epi-Gallocatechin

CAS number

970-74-1

Weight

Average: 306.2675
Monoisotopic: 306.073952802

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

Traditional IUPAC Name

epigallocatechin

Chemical Formula

C₁₅H₁₄O₇

SMILES

O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C(O)=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins 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

Substituents

Epigallocatechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
Pyrogallol derivative
Benzenetriol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:42255 )
flavan-3,3',4',5,5',7-hexol (CHEBI:42255 )
Flavans, Flavanols and Leucoanthocyanidins (C12136 )
Flavan 3-ols (C12136 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020004 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.87 g/L	ALOGPS
logP	0.71	ALOGPS
logP	1.49	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.98 m³·mol⁻¹	ChemAxon
Polarizability	29.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Bitter	FDB017700

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0978700000-567c7251027c80e91a01	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0978700000-567c7251027c80e91a01	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0940000000-a9630fe8d1a042f59c2a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0udi-3110049000-8b1040defcae8063c769	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pb9-0019003000-c4d2b02a82d1cf14714e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0pb9-0019003000-c4d2b02a82d1cf14714e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-002r-0910000000-8dfe0ba4e2ec1225213f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pb9-0019003000-c4d2b02a82d1cf14714e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-00p0-0951000000-95142c4b42b35c4bdac9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-000i-0900000000-4e9ebbe814af2f8c284d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-05r0-0913000000-be7d3c4d9b40f51414e7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0529000000-0036b0386a7ade78fcac	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00vi-0690000000-702c5a1e065692895b3a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00vi-0690000000-7844ed1a917693a67b37	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-002r-0910000000-8dfe0ba4e2ec1225213f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-00p0-0951000000-95142c4b42b35c4bdac9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-c79003b472daf421e492	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0910000000-f92cf1606a46a5b16f4f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0910000000-2026f33ac95d368b5268	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0729000000-fffbd456b9b51c7d0274	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0911000000-203a6a86214265bc09e4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ds-2900000000-023b154fc2d731ecee10	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0219000000-db1826421845ecab1485	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05n0-0922000000-86fb5a0b2fc660815604	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-2910000000-2375ce05cd5da757763c	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	42255
HMDB ID	HMDB0038361
Pubchem Compound ID	9882981
Kegg ID	C09731
ChemSpider ID	65231
FOODB ID	FDB017700
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xa4a3d230>