ChemFOnt: Showing chemical card for Apigenin 7-O-(6''-malonyl-apiosyl-glucoside) (CFc000281199)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:21 UTC

Chemfont ID

CFc000281199

Molecule Identification

Common Name

Apigenin 7-O-(6''-malonyl-apiosyl-glucoside)

Definition

Apigenin 7-o-(6''-malonyl-apiosyl-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-o-(6''-malonyl-apiosyl-glucoside) is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Apigenin 7-o-(6''-malonyl-apiosyl-glucoside) can be found in celery leaves and wild celery, which makes apigenin 7-o-(6''-malonyl-apiosyl-glucoside) a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{[(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]methoxy}oxolan-2-yl]methoxy}-3-oxopropanoate	Generator

Chemical Formula

C₂₉H₃₀O₁₇

Average Molecular Weight

650.5383

Monoisotopic Molecular Weight

650.148299534

IUPAC Name

3-{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{[(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]methoxy}oxolan-2-yl]methoxy}-3-oxopropanoic acid

Traditional Name

3-{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}oxolan-2-yl]methoxy}-3-oxopropanoic acid

CAS Registry Number

None

SMILES

O[C@@H]1[C@@H](COC(=O)CC(O)=O)O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O

InChI Identifier

InChI=1S/C29H30O17/c30-12-3-1-11(2-4-12)16-7-15(32)22-14(31)5-13(6-17(22)44-16)43-29-27(40)25(38)23(36)19(46-29)10-42-28-26(39)24(37)18(45-28)9-41-21(35)8-20(33)34/h1-7,18-19,23-31,36-40H,8-10H2,(H,33,34)/t18-,19-,23-,24-,25+,26-,27-,28-,29-/m1/s1

InChI Key

CWXBFJLEJGCTRB-PMUUMJNOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
1,3-dicarbonyl compound
Pyran
Oxane
Tetrahydrofuran
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Acetal
Ether
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301683)

Food

Herb and spice

Herb

Celery leaves (FooDB: FOOD00249)

Spice

Wild celery (FooDB: FOOD00015)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.86 g/L	ALOGPS
logP	0.6	ALOGPS
logP	-0.37	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	268.43 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	147 m³·mol⁻¹	ChemAxon
Polarizability	61.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0301683

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000148

KNApSAcK ID

Not Available

Chemspider ID

59696160

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Apigenin 7-O-(6''-malonyl-apiosyl-glucoside) (CFc000281199)

MOL for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

3D MOL for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

3D SDF for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

3D-SDF for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

PDB for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

3D PDB for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

SMILES for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

INCHI for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

Structure for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))

3D Structure for CFc000281199 (Apigenin 7-O-(6''-malonyl-apiosyl-glucoside))