ChemFOnt: Showing chemical card for 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid (CFc000281527)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:00 UTC

Chemfont ID

CFc000281527

Molecule Identification

Common Name

3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid

Definition

3-hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid, also known as amorfrutin a, is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 3-hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 3-hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid can be found in pigeon pea, which makes 3-hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Amorfrutin a	MeSH
3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylate	Generator

Chemical Formula

C₂₁H₂₄O₄

Average Molecular Weight

340.4129

Monoisotopic Molecular Weight

340.167459256

IUPAC Name

2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid

Traditional Name

2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid

CAS Registry Number

80489-90-3

SMILES

COC1=CC(CCC2=CC=CC=C2)=C(C(O)=O)C(O)=C1CC=C(C)C

InChI Identifier

InChI=1S/C21H24O4/c1-14(2)9-12-17-18(25-3)13-16(19(20(17)22)21(23)24)11-10-15-7-5-4-6-8-15/h4-9,13,22H,10-12H2,1-3H3,(H,23,24)

InChI Key

CTNFTPUIYFUXBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
P-methoxybenzoic acid or derivatives
Salicylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid or derivatives
Benzoic acid
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
Benzoyl
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302011)

Food

Pulse

Pea

Pigeon pea (FooDB: FOOD00037)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	4.37	ALOGPS
logP	6.08	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.34 m³·mol⁻¹	ChemAxon
Polarizability	37.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302011

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001743

KNApSAcK ID

C00015437

Chemspider ID

16430153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17950432

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid (CFc000281527)

MOL for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

3D MOL for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

3D SDF for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

3D-SDF for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

PDB for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

3D PDB for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

SMILES for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

INCHI for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

Structure for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)

3D Structure for CFc000281527 (3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid)