ChemFOnt: Showing chemical card for Isoswertisin 4'-rhamnoside (CFc000281392)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:44 UTC

Chemfont ID

CFc000281392

Molecule Identification

Common Name

Isoswertisin 4'-rhamnoside

Definition

Isoswertisin 4'-rhamnoside is a member of the class of compounds known as flavonoid o-glycosides. Flavonoid o-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Isoswertisin 4'-rhamnoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isoswertisin 4'-rhamnoside can be found in oat, which makes isoswertisin 4'-rhamnoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₁₄

Average Molecular Weight

592.5453

Monoisotopic Molecular Weight

592.179205732

IUPAC Name

5-hydroxy-7-methoxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)-4H-chromen-4-one

Traditional Name

5-hydroxy-7-methoxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)chromen-4-one

CAS Registry Number

83668-89-7

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)C=C1

InChI Identifier

InChI=1S/C28H32O14/c1-10-20(32)22(34)25(37)28(39-10)40-12-5-3-11(4-6-12)15-7-13(30)18-14(31)8-16(38-2)19(26(18)41-15)27-24(36)23(35)21(33)17(9-29)42-27/h3-8,10,17,20-25,27-29,31-37H,9H2,1-2H3/t10-,17+,20-,21+,22+,23-,24+,25+,27-,28-/m0/s1

InChI Key

UBQFTUKECDKZPS-UBCYTGTBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Chromone
Methoxyphenol
Benzopyran
1-benzopyran
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Oxane
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Cyclic ketone
1,2-diol
Ketone
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301876)

Food

Cereal and cereal product

Cereal

Oat (FooDB: FOOD00022)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.26 g/L	ALOGPS
logP	-0.12	ALOGPS
logP	-1.1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	141.12 m³·mol⁻¹	ChemAxon
Polarizability	57.8 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

HMDB0301876

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001560

KNApSAcK ID

Not Available

Chemspider ID

59696202

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

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Isoswertisin 4'-rhamnoside (CFc000281392)

MOL for CFc000281392 (Isoswertisin 4'-rhamnoside)

3D MOL for CFc000281392 (Isoswertisin 4'-rhamnoside)

3D SDF for CFc000281392 (Isoswertisin 4'-rhamnoside)

3D-SDF for CFc000281392 (Isoswertisin 4'-rhamnoside)

PDB for CFc000281392 (Isoswertisin 4'-rhamnoside)

3D PDB for CFc000281392 (Isoswertisin 4'-rhamnoside)

SMILES for CFc000281392 (Isoswertisin 4'-rhamnoside)

INCHI for CFc000281392 (Isoswertisin 4'-rhamnoside)

Structure for CFc000281392 (Isoswertisin 4'-rhamnoside)

3D Structure for CFc000281392 (Isoswertisin 4'-rhamnoside)