ChemFOnt: Showing chemical card for Puerarin (CFc000220529)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:41 UTC

Chemfont ID

CFc000220529

Molecule Identification

Common Name

Puerarin

Definition

Puerarin, also known as Kakonein, is a member of the class of compounds known as isoflavonoid C-glycosides. These compounds are C-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Puerarin is considered a slightly soluble (in water), acidic compound. Puerarin can be synthesized into puerarin xyloside. Puerarin is found in a number of plants and herbs, such as the root of the kudzu plant.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Daidzein 8-C-glucoside	HMDB
Kakonein	HMDB, MeSH

Chemical Formula

C₂₁H₂₀O₉

Average Molecular Weight

416.3781

Monoisotopic Molecular Weight

416.110732238

IUPAC Name

7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

puerarin

CAS Registry Number

3681-99-0

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC=C(C(=O)C2=CC=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21+/m1/s1

InChI Key

HKEAFJYKMMKDOR-VPRICQMDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid C-glycosides

Direct Parent

Isoflavonoid C-glycosides

Alternative Parents

Substituents

Isoflavonoid c-glycoside
Isoflavonoid-8-c-glycoside
Hydroxyisoflavonoid
Isoflavone
Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-glycosyl compound (CHEBI:8633 )
hydroxyisoflavone (CHEBI:8633 )
isoflavones (C10524 )
Isoflavonoids (C10524 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0240265)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.08 g/L	ALOGPS
logP	0.48	ALOGPS
logP	-0.027	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.03	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.82 m³·mol⁻¹	ChemAxon
Polarizability	41.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon