ChemFOnt: Showing chemical card for Isorhamnetin 3-beta-D-glucoside (CFc000282198)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:20 UTC

Chemfont ID

CFc000282198

Molecule Identification

Common Name

Isorhamnetin 3-beta-D-glucoside

Definition

Isorhamnetin 3-beta-d-glucoside, also known as isorhamnetin-3-glu, 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. Isorhamnetin 3-beta-d-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isorhamnetin 3-beta-d-glucoside can be synthesized from beta-D-glucose. Isorhamnetin 3-beta-d-glucoside can also be synthesized into isorhamnetin. Isorhamnetin 3-beta-d-glucoside can be found in sea-buckthornberry, which makes isorhamnetin 3-beta-d-glucoside a potential biomarker for the consumption of this food product. Isorhamnetin 3-beta-d-glucoside may be a unique S.cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Isorhamnetin-3-oglucoside	ChEMBL
Isorhamnetin 3-glucoside	ChEMBL
Isorhamnetin 3-O-beta-D-glucopyranoside	MeSH
Isorhamnetin-3-glu	MeSH
Isorhamnetin 3-b-D-glucoside	Generator
Isorhamnetin 3-β-D-glucoside	Generator
Isorhamnetin 3-O-glucoside	MeSH

Chemical Formula

C₂₂H₂₂O₁₂

Average Molecular Weight

478.4029

Monoisotopic Molecular Weight

478.111126168

IUPAC Name

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

Traditional Name

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

CAS Registry Number

None

SMILES

COC1=C(O)C=CC(=C1)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)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/t14-,16-,18+,19-,22+/m1/s1

InChI Key

CQLRUIIRRZYHHS-LFXZADKFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cadinane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302682)

Food

Fruit

Berry

Strawberry (FooDB: FOOD00083)
Sea-buckthornberry (FooDB: FOOD00087)

Process

Not Available

Role

Not Available

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)	6.44	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	45.4 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

HMDB0302682

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005749

KNApSAcK ID

C00005525

Chemspider ID

4477169

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

75750

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Isorhamnetin 3-beta-D-glucoside (CFc000282198)

MOL for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

3D MOL for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

3D SDF for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

3D-SDF for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

PDB for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

3D PDB for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

SMILES for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

INCHI for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

Structure for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)

3D Structure for CFc000282198 (Isorhamnetin 3-beta-D-glucoside)