Identification

PhytoHub ID
PHUB000262
Name
(-)-Epicatechin
Systematic Name
(−)-Epicatechin
Synonyms
  • (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
  • 3,5,7,3',4'-Pentahydroxyflavane
  • Epicatechol
CAS Number
490-46-0
Average Mass
290.271
Monoisotopic Mass
290.079038171
Chemical Formula
C15H14O6
IUPAC Name
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI Key
PFTAWBLQPZVEMU-UKRRQHHQSA-N
InChI Identifier
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
SMILES
O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O
Structure

Calculated Properties

Solubility (ALOGPS)
6.45e-01 g/l
LogS (ALOGPS)
-2.65
LogP (ALOGPS)
1.02
Hydrogen Acceptors
6
Hydrogen Donors
5
Rotatable Bond Count
1
Polar Surface Area
110.38000000000001
Refractivity
73.99970000000002
Polarizability
28.70641069763134
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-3.2897193322428566
pKa (strongest acidic)
9.004573813837975
Number of Rings
3
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavan-3-ols

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Flavonoid metabolites
Metabolite Sub-class
Flavan-3-ols (parent and host metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Procyanidin dimer B2PolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
(-)-EpicatechinPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavans
Direct Parent Name
Catechins
Alternative Parent Names
["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "3-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "Benzene and substituted derivatives", "Catechols", "Hydrocarbon derivatives", "Oxacyclic compounds", "Polyols", "Secondary alcohols"]
External Descriptor Annotations
["Condensed tannins (Proanthocyanidins)", "Flavan 3-ols", "Flavans, Flavanols and Leucoanthocyanidins", "catechin", "polyphenol"]
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "3-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Alcohol", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Catechin", "Catechol", "Chromane", "Ether", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Polyol", "Secondary alcohol"]

Spectra from Phytohub

Food Sources

Food Sources of its Food Phytochemical(s)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

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