ChemFOnt: Showing chemical card for Kaempferol 3-gentiobioside (CFc000283122)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:06 UTC

Chemfont ID

CFc000283122

Molecule Identification

Common Name

Kaempferol 3-gentiobioside

Definition

Kaempferol 3-gentiobioside is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-gentiobioside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-gentiobioside can be found in soy bean, which makes kaempferol 3-gentiobioside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-beta-D-glucosyl-beta-D-glucoside	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucosyl-(1->6)-beta-D-glucoside	ChEBI
Kaempferol 3-gentiobioside	ChEBI
Kaempferol 3-O-beta-gentiobioside	ChEBI
Kaempferol 3-O-gentiobioside	ChEBI
Kaempferol beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside	ChEBI
Kaempferol beta-D-glucosyl-(1->6)-beta-D-glucoside	ChEBI
Kaempferol-3-gentiobioside	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-b-D-glucosyl-b-D-glucoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-β-D-glucosyl-β-D-glucoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl b-D-glucopyranosyl-(1->6)-b-D-glucopyranoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl b-D-glucosyl-(1->6)-b-D-glucoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl β-D-glucosyl-(1->6)-β-D-glucoside	Generator
Kaempferol 3-O-b-gentiobioside	Generator
Kaempferol 3-O-β-gentiobioside	Generator
Kaempferol b-D-glucopyranosyl-(1->6)-b-D-glucopyranoside	Generator
Kaempferol β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside	Generator
Kaempferol b-D-glucosyl-(1->6)-b-D-glucoside	Generator
Kaempferol β-D-glucosyl-(1->6)-β-D-glucoside	Generator
Kaempferol 3-b-gentiobioside	Generator
Kaempferol 3-β-gentiobioside	Generator

Chemical Formula

C₂₇H₃₀O₁₆

Average Molecular Weight

610.5175

Monoisotopic Molecular Weight

610.153384912

IUPAC Name

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

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

22149-35-5

SMILES

OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-8-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-12(31)5-11(30)6-13(16)40-24(25)9-1-3-10(29)4-2-9/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1

InChI Key

BITPRCODIALMOV-DEFKTLOSSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303606)

Food

Soy

Soy bean (FooDB: FOOD00085)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.19 g/L	ALOGPS
logP	-0.55	ALOGPS
logP	-1.6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.71 m³·mol⁻¹	ChemAxon
Polarizability	57.53 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

HMDB0303606

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016664

KNApSAcK ID

C00005166

Chemspider ID

8136119

KEGG Compound ID

Not Available

BioCyc ID

CPD-14847

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

136785

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Kaempferol 3-gentiobioside (CFc000283122)

MOL for CFc000283122 (Kaempferol 3-gentiobioside)

3D MOL for CFc000283122 (Kaempferol 3-gentiobioside)

3D SDF for CFc000283122 (Kaempferol 3-gentiobioside)

3D-SDF for CFc000283122 (Kaempferol 3-gentiobioside)

PDB for CFc000283122 (Kaempferol 3-gentiobioside)

3D PDB for CFc000283122 (Kaempferol 3-gentiobioside)

SMILES for CFc000283122 (Kaempferol 3-gentiobioside)

INCHI for CFc000283122 (Kaempferol 3-gentiobioside)

Structure for CFc000283122 (Kaempferol 3-gentiobioside)

3D Structure for CFc000283122 (Kaempferol 3-gentiobioside)