ChemFOnt: Showing chemical card for Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside (CFc000281198)

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

CFc000281198

Molecule Identification

Common Name

Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside

Definition

Luteolin 7-o-(2-apiosyl-6-malonyl)-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. Luteolin 7-o-(2-apiosyl-6-malonyl)-glucoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Luteolin 7-o-(2-apiosyl-6-malonyl)-glucoside can be found in a number of food items such as italian sweet red pepper, pepper (c. annuum), wild celery, and celery leaves, which makes luteolin 7-o-(2-apiosyl-6-malonyl)-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₉H₃₀O₁₈

Average Molecular Weight

666.5377

Monoisotopic Molecular Weight

666.143214156

IUPAC Name

3-{[(2R,3S,4S,5R,6S)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4-dihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid

Traditional Name

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

CAS Registry Number

None

SMILES

OC[C@@]1(O)CO[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C(O)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C29H30O18/c30-9-29(41)10-43-28(26(29)40)47-25-24(39)23(38)19(8-42-21(37)7-20(35)36)46-27(25)44-12-4-15(33)22-16(34)6-17(45-18(22)5-12)11-1-2-13(31)14(32)3-11/h1-6,19,23-28,30-33,38-41H,7-10H2,(H,35,36)/t19-,23-,24+,25-,26+,27-,28+,29-/m1/s1

InChI Key

LPOQROCPKZWCGK-CQRLEKJLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glucuronides

Alternative Parents

Substituents

Flavonoid-3-o-glucuronide
Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monocyclic benzene moiety
Oxane
Hydroxy acid
Benzenoid
Vinylogous acid
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301682)

Food

Herb and spice

Herb

Celery leaves (FooDB: FOOD00249)

Spice

Wild celery (FooDB: FOOD00015)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.04 g/L	ALOGPS
logP	0.51	ALOGPS
logP	-0.81	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	288.66 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	149.2 m³·mol⁻¹	ChemAxon
Polarizability	62.81 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

HMDB0301682

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000144

KNApSAcK ID

Not Available

Chemspider ID

59696159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102130970

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside (CFc000281198)

MOL for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

3D MOL for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

3D SDF for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

3D-SDF for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

PDB for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

3D PDB for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

SMILES for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

INCHI for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

Structure for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)

3D Structure for CFc000281198 (Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside)