ChemFOnt: Showing chemical card for Isorhamnetin 3-O-b-D-glucopyranoside (CFc000336865)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:15 UTC

Chemfont ID

CFc000336865

Molecule Identification

Common Name

Isorhamnetin 3-O-b-D-glucopyranoside

Definition

Isorhamnetin 3-o-b-d-glucopyranoside, also known as isorhamnetin-3-O-galactoside, 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. Thus, isorhamnetin 3-o-b-d-glucopyranoside is considered to be a flavonoid lipid molecule. Isorhamnetin 3-o-b-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isorhamnetin 3-o-b-d-glucopyranoside can be found in a number of food items such as common grape, caraway, ginkgo nuts, and grape wine, which makes isorhamnetin 3-o-b-d-glucopyranoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Isorhamnetin-3-O-galactoside	HMDB

Chemical Formula

C₂₂H₂₂O₁₂

Average Molecular Weight

478.4029

Monoisotopic Molecular Weight

478.111126168

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

isorhamnetin 3-galactoside

CAS Registry Number

5041-82-7

SMILES

COC1=C(O)C=CC(=C1)C1=C(OC2OC(CO)C(O)C(O)C2O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3

InChI Key

CQLRUIIRRZYHHS-UHFFFAOYSA-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
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112315 )

Functional Ontology

Not Available

Endogenous (FooDB: )

Plant

Plant (FooDB: )

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Tropical fruit

Guava (FooDB: FOOD00150)

Berry

Common grape (FooDB: FOOD00204)
Sea-buckthornberry (FooDB: FOOD00087)

Herb and spice

Herb

Chives (FooDB: FOOD00009)
Mugwort (FooDB: FOOD00020)

Spice

Caraway (FooDB: FOOD00043)

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Vegetable

Leaf vegetable

Rocket salad (ssp.) (FooDB: FOOD00077)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Pulse

Other pulse

White lupine (FooDB: FOOD00403)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Hepatoprotective (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	0.64	ALOGPS
logP	0.0011	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.76 m³·mol⁻¹	ChemAxon
Polarizability	45.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0126573

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021629

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13245586

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Isorhamnetin 3-O-b-D-glucopyranoside (CFc000336865)

MOL for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

3D MOL for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

3D SDF for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

3D-SDF for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

PDB for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

3D PDB for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

SMILES for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

INCHI for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

Structure for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)

3D Structure for CFc000336865 (Isorhamnetin 3-O-b-D-glucopyranoside)