ChemFOnt: Showing chemical card for Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl (CFc000334071)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:14:50 UTC

Chemfont ID

CFc000334071

Molecule Identification

Common Name

Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl

Definition

Kaempferol 3-rhamno-glucoside, also known as nicotiflorin or kaempferol 3-rutinoside, 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-rhamno-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-rhamno-glucoside can be found in ginkgo nuts and tea, which makes kaempferol 3-rhamno-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Kaempferol 3-O-(6''-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside	ChEBI
Kaempferol-3-O-beta-rutinoside	ChEBI
Nicotiflorin	ChEBI
3-((6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	Generator
3-((6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	Generator
Kaempferol 3-O-(6''-O-a-L-rhamnopyranosyl)-b-D-glucopyranoside	Generator
Kaempferol 3-O-(6''-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside	Generator
Kaempferol-3-O-b-rutinoside	Generator
Kaempferol-3-O-β-rutinoside	Generator
Kaempferol-3-O-alpha-L-rhamanopyranosyl-(1'''-6'')-beta-D-glucopyranoside	MeSH
Kaempferol-3-O-rhamanopyranosyl-(1'''-6'')-glucopyranoside	MeSH

Chemical Formula

C₂₇H₃₀O₁₅

Average Molecular Weight

594.5181

Monoisotopic Molecular Weight

594.15847029

IUPAC Name

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

CAS Registry Number

17650-84-9

SMILES

C[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/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

rutinoside (CHEBI:69657 )
disaccharide derivative (CHEBI:69657 )
trihydroxyflavone (CHEBI:69657 )
kaempferol O-glucoside (CHEBI:69657 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Nut

Almond (FooDB: FOOD00148)

Fruit

Drupe

Apricot (FooDB: FOOD00144)

Berry

Strawberry (FooDB: FOOD00083)

Pulse

Lentil

Lentils (FooDB: FOOD00098)

Tea

Black tea (FooDB: FOOD00907)
Green tea (FooDB: FOOD00908)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.07 g/L	ALOGPS
logP	0.07	ALOGPS
logP	-0.57	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	138.16 m³·mol⁻¹	ChemAxon
Polarizability	56.68 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

HMDB0302426

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005905

KNApSAcK ID

C00005169

Chemspider ID

4477257

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318767

PDB ID

Not Available

ChEBI ID

69657

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl (CFc000334071)

MOL for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

3D MOL for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

3D SDF for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

3D-SDF for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

PDB for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

3D PDB for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

SMILES for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

INCHI for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

Structure for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)

3D Structure for CFc000334071 (Kaempferol 3-O-alpha-L-rhamnoside-beta-D-glucosyl)