ChemFOnt: Showing chemical card for Procyanidin C (CFc000336890)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:18 UTC

Chemfont ID

CFc000336890

Molecule Identification

Common Name

Procyanidin C

Definition

Ent-epicatechin(4alpha->8)catechin, also known as procyanidin b, 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''. Ent-epicatechin(4alpha->8)catechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ent-epicatechin(4alpha->8)catechin can be found in sago palm, which makes ent-epicatechin(4alpha->8)catechin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
ent-Epicatechin(4a->8)catechin	Generator
ent-Epicatechin(4α->8)catechin	Generator
ent-Epicatechin-(4alpha->8)-catechin	HMDB
Procyanidin b	MeSH, HMDB
ent-Epicatechin-(4a->8)-catechin	Generator
ent-Epicatechin-(4α->8)-catechin	Generator

Chemical Formula

C₃₀H₂₆O₁₂

Average Molecular Weight

578.5202

Monoisotopic Molecular Weight

578.142426296

IUPAC Name

2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

proanthocyanidin B1

CAS Registry Number

35356-33-3

SMILES

OC1CC2=C(O)C=C(O)C(C3C(O)C(OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2OC1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2

InChI Key

XFZJEEAOWLFHDH-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

B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
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

a small molecule (CPD-7631 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0037968)

Food

Vegetable

Fruit vegetable

Avocado (FooDB: FOOD00130)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0037968)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.29	ALOGPS
logP	3.12	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	220.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	146.51 m³·mol⁻¹	ChemAxon
Polarizability	56.91 Å³	ChemAxon
Number of Rings	6	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

HMDB0037968

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017144

KNApSAcK ID

C00009078

Chemspider ID

115490

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

130556

PDB ID

Not Available

ChEBI ID

173294

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Procyanidin C (CFc000336890)

MOL for CFc000336890 (Procyanidin C)

3D MOL for CFc000336890 (Procyanidin C)

3D SDF for CFc000336890 (Procyanidin C)

3D-SDF for CFc000336890 (Procyanidin C)

PDB for CFc000336890 (Procyanidin C)

3D PDB for CFc000336890 (Procyanidin C)

SMILES for CFc000336890 (Procyanidin C)

INCHI for CFc000336890 (Procyanidin C)

Structure for CFc000336890 (Procyanidin C)

3D Structure for CFc000336890 (Procyanidin C)