ChemFOnt: Showing chemical card for 4',5,7-Trihydroxyflavanol (CFc000336904)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:19 UTC

Chemfont ID

CFc000336904

Molecule Identification

Common Name

4',5,7-Trihydroxyflavanol

Definition

Afzelechin is a member of the class of compounds known as flavan-3-ols. Flavan-3-ols are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. Afzelechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Afzelechin can be found in kiwi and peach, which makes afzelechin a potential biomarker for the consumption of these food products. Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in Bergenia ligulata (a.k.a. Paashaanbhed in Ayurveda traditional Indian medicine). It exists as at least 2 major epimers (afzelechin and epi-afzelechin) .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-3,4',5,7-Flaventetrol	HMDB
(+)-Afzelechin	HMDB
3,5,7,4'-Tetrahydroxyflavan	HMDB

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

3,5,7,4'-tetrahydroxyflavan

CAS Registry Number

117-39-5

SMILES

OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2

InChI Key

RSYUFYQTACJFML-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
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
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a 2,3-<i>trans</i>-flavan-3-ol (CPD-1962 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0005794)

Food

Fruit

Drupe

Peach (FooDB: FOOD00149)

Process

Not Available

Role

Biological role

Allelopathic (HMDB: HMDB0005794)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	1.29	ALOGPS
logP	2.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	27.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030823

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021730

KNApSAcK ID

C00000937

Chemspider ID

248333

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Afzelechin

METLIN ID

Not Available

PubChem Compound

282014

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4',5,7-Trihydroxyflavanol (CFc000336904)

MOL for CFc000336904 (4',5,7-Trihydroxyflavanol)

3D MOL for CFc000336904 (4',5,7-Trihydroxyflavanol)

3D SDF for CFc000336904 (4',5,7-Trihydroxyflavanol)

3D-SDF for CFc000336904 (4',5,7-Trihydroxyflavanol)

PDB for CFc000336904 (4',5,7-Trihydroxyflavanol)

3D PDB for CFc000336904 (4',5,7-Trihydroxyflavanol)

SMILES for CFc000336904 (4',5,7-Trihydroxyflavanol)

INCHI for CFc000336904 (4',5,7-Trihydroxyflavanol)

Structure for CFc000336904 (4',5,7-Trihydroxyflavanol)

3D Structure for CFc000336904 (4',5,7-Trihydroxyflavanol)