ChemFOnt: Showing chemical card for Proanthocyanidin A7 (CFc000336705)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:00 UTC

Chemfont ID

CFc000336705

Molecule Identification

Common Name

Proanthocyanidin A7

Definition

Epicatechin-(2beta->5,4beta->6)-ent-epicatechin is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Epicatechin-(2beta->5,4beta->6)-ent-epicatechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epicatechin-(2beta->5,4beta->6)-ent-epicatechin can be found in cocoa bean, which makes epicatechin-(2beta->5,4beta->6)-ent-epicatechin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Epicatechin-(2b->5,4b->6)-ent-epicatechin	Generator
Epicatechin-(2β->5,4β->6)-ent-epicatechin	Generator
Epicatechin-(2b->5,4b->6)ent-epicatechin	HMDB

Chemical Formula

C₃₀H₂₄O₁₂

Average Molecular Weight

576.5044

Monoisotopic Molecular Weight

576.126776232

IUPAC Name

7,13-bis(3,4-dihydroxyphenyl)-6,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]henicosa-2,4,10,15(20),16,18-hexaene-3,8,17,19,21-pentol

Traditional Name

7,13-bis(3,4-dihydroxyphenyl)-6,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]henicosa-2,4,10,15(20),16,18-hexaene-3,8,17,19,21-pentol

CAS Registry Number

114569-32-3

SMILES

OC1CC2=C3OC4(OC5=C(C(C4O)C3=C(O)C=C2OC1C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C5)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H24O12/c31-13-7-19(36)24-23(8-13)41-30(12-2-4-16(33)18(35)6-12)29(39)26(24)25-20(37)10-22-14(28(25)42-30)9-21(38)27(40-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26-27,29,31-39H,9H2

InChI Key

SHYPVJZSIOEHJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Pyranoflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Pyranochromene
1-benzopyran
Chromane
Benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketal
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Ether
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0040678)
Extracellular (HMDB: HMDB0040678)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040678)

Source

Exogenous

Exogenous (HMDB: HMDB0040678)

Food

Food (HMDB: HMDB0040678)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Plant

Plant (HMDB: HMDB0040678)
Theobroma cacao (HMDB: HMDB0040678)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040678)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.44	ALOGPS
logP	3.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	209.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.2 m³·mol⁻¹	ChemAxon
Polarizability	57.16 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040678

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020475

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14841178

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Proanthocyanidin A7 (CFc000336705)

MOL for CFc000336705 (Proanthocyanidin A7)

3D MOL for CFc000336705 (Proanthocyanidin A7)

3D SDF for CFc000336705 (Proanthocyanidin A7)

3D-SDF for CFc000336705 (Proanthocyanidin A7)

PDB for CFc000336705 (Proanthocyanidin A7)

3D PDB for CFc000336705 (Proanthocyanidin A7)

SMILES for CFc000336705 (Proanthocyanidin A7)

INCHI for CFc000336705 (Proanthocyanidin A7)

Structure for CFc000336705 (Proanthocyanidin A7)

3D Structure for CFc000336705 (Proanthocyanidin A7)