ChemFOnt: Showing chemical card for Apigenin 7-(6''-O-acetyl)-glucoside (CFc000282250)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:26 UTC

Chemfont ID

CFc000282250

Molecule Identification

Common Name

Apigenin 7-(6''-O-acetyl)-glucoside

Definition

Apigenin 7-(6''-o-acetyl)-glucoside is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apigenin 7-(6''-o-acetyl)-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apigenin 7-(6''-o-acetyl)-glucoside can be found in german camomile, which makes apigenin 7-(6''-o-acetyl)-glucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₃H₂₂O₁₁

Average Molecular Weight

474.4142

Monoisotopic Molecular Weight

474.116211546

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

520-36-5

SMILES

CC(=O)OC[C@H]1O[C@@H](OC2=CC3=C(C(O)=C2)C(=O)C=C(O3)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H22O11/c1-10(24)31-9-18-20(28)21(29)22(30)23(34-18)32-13-6-14(26)19-15(27)8-16(33-17(19)7-13)11-2-4-12(25)5-3-11/h2-8,18,20-23,25-26,28-30H,9H2,1H3/t18-,20-,21+,22-,23-/m1/s1

InChI Key

LYFXRHUNCZZUTQ-DODNOZFWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:81340 )
flavonols (CHEBI:81340 )
dimethoxyflavone (CHEBI:81340 )
Flavones and Flavonols (C17788 )
Flavones and Flavonols (LMPK12112994 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302734)

Food

Herb and spice

Herb

German camomile (FooDB: FOOD00107)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	1.26	ALOGPS
logP	0.88	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.21 m³·mol⁻¹	ChemAxon
Polarizability	46.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0302734

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005983

KNApSAcK ID

Not Available

Chemspider ID

10306105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21721966

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Apigenin 7-(6''-O-acetyl)-glucoside (CFc000282250)

MOL for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

3D MOL for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

3D SDF for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

3D-SDF for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

PDB for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

3D PDB for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

SMILES for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

INCHI for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

Structure for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)

3D Structure for CFc000282250 (Apigenin 7-(6''-O-acetyl)-glucoside)