ChemFOnt: Showing chemical card for Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin (CFc000282578)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:04 UTC

Chemfont ID

CFc000282578

Molecule Identification

Common Name

Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin

Definition

Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin 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-(4beta->8)-epicatechin-(4beta->6)-catechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin can be found in common grape, which makes epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin	ChEBI
Epicatechin-(4b->8)-epicatechin-(4b->6)-catechin	Generator
Epicatechin-(4β->8)-epicatechin-(4β->6)-catechin	Generator

Chemical Formula

C₄₅H₃₈O₁₈

Average Molecular Weight

866.7724

Monoisotopic Molecular Weight

866.205814412

IUPAC Name

(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

arecatannin B1

CAS Registry Number

None

SMILES

O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C=C(O)C([C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3[C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)=C2O

InChI Identifier

InChI=1S/C45H38O18/c46-18-10-26(53)33-32(11-18)62-43(16-2-5-21(48)24(51)8-16)40(59)37(33)35-27(54)13-28(55)36-38(41(60)44(63-45(35)36)17-3-6-22(49)25(52)9-17)34-29(56)14-31-19(39(34)58)12-30(57)42(61-31)15-1-4-20(47)23(50)7-15/h1-11,13-14,30,37-38,40-44,46-60H,12H2/t30-,37+,38-,40+,41+,42+,43+,44+/m0/s1

InChI Key

PBYRKMXDROOXMU-XKDUFCMJSA-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

polyphenol (CHEBI:75642 )
proanthocyanidin (CHEBI:75642 )
hydroxyflavan (CHEBI:75642 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303062)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	3.38	ALOGPS
logP	4.44	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	331.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	219.02 m³·mol⁻¹	ChemAxon
Polarizability	85.86 Å³	ChemAxon
Number of Rings	9	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

HMDB0303062

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007562

KNApSAcK ID

Not Available

Chemspider ID

10290128

KEGG Compound ID

C17892

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Arecatannin_B1

METLIN ID

Not Available

PubChem Compound

14237657

PDB ID

Not Available

ChEBI ID

75642

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin (CFc000282578)

MOL for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D MOL for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D SDF for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D-SDF for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

PDB for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D PDB for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

SMILES for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

INCHI for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

Structure for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)

3D Structure for CFc000282578 (Epicatechin-(4beta->8)-epicatechin-(4beta->6)-catechin)