ChemFOnt: Showing chemical card for Kaempferol 3-rhamnoside (CFc000336128)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:29:05 UTC

Chemfont ID

CFc000336128

Molecule Identification

Common Name

Kaempferol 3-rhamnoside

Definition

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one 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. 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one can be found in a number of food items such as endive, linden, peach, and ginkgo nuts, which makes 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Kaempferol-3-O-alpha-L-rhamnoside	MeSH, HMDB
Kaempferol-3-rhamnoside	MeSH, HMDB
Deacyl-SL0101	MeSH, HMDB

Chemical Formula

C₂₁H₂₀O₁₀

Average Molecular Weight

432.3775

Monoisotopic Molecular Weight

432.10564686

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one

CAS Registry Number

482-39-3

SMILES

CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3

InChI Key

SOSLMHZOJATCCP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Alkyl halide
Alkyl chloride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (FooDB: )

Plant

Plant (FooDB: )

Lettuce (FooDB: FOOD00095)
Endive (FooDB: FOOD00048)

Fruit

Tropical fruit

Kiwi (FooDB: FOOD00004)

Drupe

Peach (FooDB: FOOD00149)

Herb and spice

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Herb

Linden (FooDB: FOOD00184)

Nut

Common hazelnut (FooDB: FOOD00062)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Flavone and Flavonol Biosynthesis (PathBank: SMP0012025)

EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (FooDB: )
EC 1.1.1.21 (aldehyde reductase) inhibitor (FooDB: )

Enzyme inhibitor

Angiotensin converting enzyme inhibitor (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.55 g/L	ALOGPS
logP	1.48	ALOGPS
logP	1.21	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.75 m³·mol⁻¹	ChemAxon
Polarizability	41.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0253754

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016491

KNApSAcK ID

C00005186

Chemspider ID

4717304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Afzelin

METLIN ID

Not Available

PubChem Compound

5835713

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Kaempferol 3-rhamnoside (CFc000336128)

MOL for CFc000336128 (Kaempferol 3-rhamnoside)

3D MOL for CFc000336128 (Kaempferol 3-rhamnoside)

3D SDF for CFc000336128 (Kaempferol 3-rhamnoside)

3D-SDF for CFc000336128 (Kaempferol 3-rhamnoside)

PDB for CFc000336128 (Kaempferol 3-rhamnoside)

3D PDB for CFc000336128 (Kaempferol 3-rhamnoside)

SMILES for CFc000336128 (Kaempferol 3-rhamnoside)

INCHI for CFc000336128 (Kaempferol 3-rhamnoside)

Structure for CFc000336128 (Kaempferol 3-rhamnoside)

3D Structure for CFc000336128 (Kaempferol 3-rhamnoside)