ChemFOnt: Showing chemical card for 3-O-Methylkaempferol (CFc000282080)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:05 UTC

Chemfont ID

CFc000282080

Molecule Identification

Common Name

3-O-Methylkaempferol

Definition

3-o-methylkaempferol, also known as 5,7,4'-trihydroxy-3-methoxyflavone or isokaempferide, is a member of the class of compounds known as 3-o-methylated flavonoids. 3-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, 3-o-methylkaempferol is considered to be a flavonoid lipid molecule. 3-o-methylkaempferol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 3-o-methylkaempferol can be found in common bean and coriander, which makes 3-o-methylkaempferol a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-Methylkaempferol	ChEBI
5,7,4'-Trihydroxy-3-methoxyflavone	ChEBI
Isokaempferide	ChEBI
Kaempferol-3-O-methyl ether	ChEBI

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one

Traditional Name

isokaempferide

CAS Registry Number

1592-70-7

SMILES

COC1=C(OC2=C(C(O)=CC(O)=C2)C1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O6/c1-21-16-14(20)13-11(19)6-10(18)7-12(13)22-15(16)8-2-4-9(17)5-3-8/h2-7,17-19H,1H3

InChI Key

VJJZJBUCDWKPLC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:1579 )
trihydroxyflavone (CHEBI:1579 )
flavonols (C05902 )
Flavones and Flavonols (LMPK12112688 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302564)

Food

Pulse

Bean

Common bean (FooDB: FOOD00134)

Herb and spice

Herb

Coriander (FooDB: FOOD00061)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.077 g/L	ALOGPS
logP	3.08	ALOGPS
logP	2.57	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.63 m³·mol⁻¹	ChemAxon
Polarizability	29.49 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