ChemFOnt: Showing chemical card for Meloside (CFc000282099)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:08 UTC

Chemfont ID

CFc000282099

Molecule Identification

Common Name

Meloside

Definition

Meloside, also known as isovitexin 2''-beta-D-O-glucoside or 2'-O-beta-D-glucosylisovitexin, is a member of the class of 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. Meloside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Meloside can be found in muskmelon, which makes meloside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2'-O-beta-D-Glucosylisovitexin	ChEBI
Isovitexin 2''-beta-D-O-glucoside	ChEBI
Isovitexin 2''-O-glucoside	ChEBI
Meloside a	ChEBI
2'-O-b-D-Glucosylisovitexin	Generator
2'-O-Β-D-glucosylisovitexin	Generator
Isovitexin 2''-b-D-O-glucoside	Generator
Isovitexin 2''-β-D-O-glucoside	Generator
2''-O-(b-D-Glucosyl)isovitexin	Generator
2''-O-(Β-D-glucosyl)isovitexin	Generator
Isovitexin 2''-O-b-D-glucoside	Generator
Isovitexin 2''-O-β-D-glucoside	Generator
Isovitexin 2''-O-beta-glucoside	MeSH

Chemical Formula

C₂₇H₃₀O₁₅

Average Molecular Weight

594.5181

Monoisotopic Molecular Weight

594.15847029

IUPAC Name

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

Traditional Name

isovitexin 2''-O-β-D-glucoside

CAS Registry Number

60767-80-8

SMILES

OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2C2=C(O)C=C3OC(=CC(=O)C3=C2O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H30O15/c28-7-15-20(34)23(37)26(42-27-24(38)22(36)19(33)16(8-29)41-27)25(40-15)18-12(32)6-14-17(21(18)35)11(31)5-13(39-14)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25+,26-,27+/m1/s1

InChI Key

RQTTXGQDIROLTQ-FASGCTRLSA-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
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl 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

disaccharide derivative (CHEBI:75432 )
C-glycosyl compound (CHEBI:75432 )
trihydroxyflavone (CHEBI:75432 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302583)

Food

Gourd

Muskmelon (FooDB: FOOD00064)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.26 g/L	ALOGPS
logP	-0.67	ALOGPS
logP	-1.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	256.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	138.45 m³·mol⁻¹	ChemAxon
Polarizability	56.96 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

HMDB0302583

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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

75432

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Meloside (CFc000282099)

MOL for CFc000282099 (Meloside)

3D MOL for CFc000282099 (Meloside)

3D SDF for CFc000282099 (Meloside)

3D-SDF for CFc000282099 (Meloside)

PDB for CFc000282099 (Meloside)

3D PDB for CFc000282099 (Meloside)

SMILES for CFc000282099 (Meloside)

INCHI for CFc000282099 (Meloside)

Structure for CFc000282099 (Meloside)

3D Structure for CFc000282099 (Meloside)