ChemFOnt: Showing chemical card for Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside (CFc000281470)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:53 UTC

Chemfont ID

CFc000281470

Molecule Identification

Common Name

Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside

Definition

Luteolin 7-o-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside 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. Thus, luteolin 7-o-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside is considered to be a flavonoid lipid molecule. Luteolin 7-o-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Luteolin 7-o-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside can be found in a number of food items such as yellow bell pepper, green bell pepper, italian sweet red pepper, and red bell pepper, which makes luteolin 7-o-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-{[(3S,4S,6S)-5-{[(2S,3S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-4-hydroxy-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-3-oxopropanoate	Generator

Chemical Formula

C₃₅H₄₀O₂₃

Average Molecular Weight

828.682

Monoisotopic Molecular Weight

828.196037548

IUPAC Name

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

Traditional Name

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

CAS Registry Number

612844-31-2

SMILES

[H][C@@]1(OC2([H])[C@]([H])(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC(O)=C(O)C=C3)OC([H])(COC(=O)CC(O)=O)[C@@]([H])(O[C@]3([H])OC([H])(CO)[C@@]([H])(O)[C@]([H])(O)C3([H])O)[C@]2([H])O)OCC(O)(CO)[C@]1([H])O

InChI Identifier

InChI=1S/C35H40O23/c36-8-20-25(45)26(46)27(47)32(55-20)57-29-21(9-51-23(44)7-22(42)43)56-33(30(28(29)48)58-34-31(49)35(50,10-37)11-52-34)53-13-4-16(40)24-17(41)6-18(54-19(24)5-13)12-1-2-14(38)15(39)3-12/h1-6,20-21,25-34,36-40,45-50H,7-11H2,(H,42,43)/t20?,21?,25-,26+,27?,28+,29-,30?,31-,32+,33-,34+,35?/m1/s1

InChI Key

UAGBVLJNVRPERW-GGBSEEMMSA-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110705 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301954)

Food

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.54 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-2.6	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	367.81 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	181.62 m³·mol⁻¹	ChemAxon
Polarizability	77.91 Å³	ChemAxon
Number of Rings	6	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

HMDB0301954

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001668

KNApSAcK ID

Not Available

Chemspider ID

24843735

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 Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside (CFc000281470)

MOL for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

3D MOL for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

3D SDF for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

3D-SDF for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

PDB for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

3D PDB for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

SMILES for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

INCHI for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

Structure for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)

3D Structure for CFc000281470 (Luteolin 7-O-(2-apiofuranosyl-4-glucopyranosyl-6-malonyl)glucopyranoside)