ChemFOnt: Showing chemical card for Isorhamnetin 3-rutinoside (CFc000332923)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:32 UTC

Chemfont ID

CFc000332923

Molecule Identification

Common Name

Isorhamnetin 3-rutinoside

Definition

Isorhamnetin 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. Isorhamnetin 3-rutinoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isorhamnetin 3-rutinoside can be found in common bean, ginkgo nuts, sea-buckthornberry, and swede, which makes isorhamnetin 3-rutinoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
I-rha-gal	HMDB
Isorhamnetin 3-robinobioside	HMDB
Narcissin	MeSH
Narcissin flavonol	MeSH

Chemical Formula

C₂₈H₃₂O₁₆

Average Molecular Weight

624.5441

Monoisotopic Molecular Weight

624.169034976

IUPAC Name

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

CAS Registry Number

604-80-8

SMILES

COC1=CC(=CC=C1O)C1=C(OC2OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C2O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3

InChI Key

UIDGLYUNOUKLBM-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
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
1-benzopyran
Methoxyphenol
Benzopyran
Phenol ether
Phenoxy compound
Anisole
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0037746)
Extracellular (HMDB: HMDB0037746)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037746)

Source

Exogenous

Exogenous (HMDB: HMDB0037746)

Food

Food (HMDB: HMDB0037746)

Pulse

Bean

Common bean (FooDB: FOOD00134)

Fruit

Pome

Pear (FooDB: FOOD00152)
Asian pear (FooDB: FOOD00291)

Berry

Sea-buckthornberry (FooDB: FOOD00087)

Vegetable

Root vegetable

Swede (FooDB: FOOD00028)

Herb and spice

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Endogenous

Plant

Plant (HMDB: HMDB0037746)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037746)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.8 g/L	ALOGPS
logP	0.16	ALOGPS
logP	-0.72	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	254.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	144.63 m³·mol⁻¹	ChemAxon
Polarizability	59.65 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

HMDB0037746

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000609

KNApSAcK ID

C00005538

Chemspider ID

4851695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6223069

PDB ID

Not Available

ChEBI ID

139417

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Isorhamnetin 3-rutinoside (CFc000332923)

MOL for CFc000332923 (Isorhamnetin 3-rutinoside)

3D MOL for CFc000332923 (Isorhamnetin 3-rutinoside)

3D SDF for CFc000332923 (Isorhamnetin 3-rutinoside)

3D-SDF for CFc000332923 (Isorhamnetin 3-rutinoside)

PDB for CFc000332923 (Isorhamnetin 3-rutinoside)

3D PDB for CFc000332923 (Isorhamnetin 3-rutinoside)

SMILES for CFc000332923 (Isorhamnetin 3-rutinoside)

INCHI for CFc000332923 (Isorhamnetin 3-rutinoside)

Structure for CFc000332923 (Isorhamnetin 3-rutinoside)

3D Structure for CFc000332923 (Isorhamnetin 3-rutinoside)