ChemFOnt: Showing chemical card for Isovitexin 7-(6'''-(E)-p-coumaroylglucoside) (CFc000281491)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:55 UTC

Chemfont ID

CFc000281491

Molecule Identification

Common Name

Isovitexin 7-(6'''-(E)-p-coumaroylglucoside)

Definition

Isovitexin 7-(6'''-(e)-p-coumaroylglucoside) is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Isovitexin 7-(6'''-(e)-p-coumaroylglucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Isovitexin 7-(6'''-(e)-p-coumaroylglucoside) can be found in barley, which makes isovitexin 7-(6'''-(e)-p-coumaroylglucoside) a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₆H₃₆O₁₇

Average Molecular Weight

740.6608

Monoisotopic Molecular Weight

740.195249726

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

496788-49-9

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C=C2)C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C36H36O17/c37-13-23-28(42)31(45)33(47)35(51-23)27-22(12-21-26(30(27)44)19(40)11-20(50-21)16-4-8-18(39)9-5-16)52-36-34(48)32(46)29(43)24(53-36)14-49-25(41)10-3-15-1-6-17(38)7-2-15/h1-12,23-24,28-29,31-39,42-48H,13-14H2/b10-3+/t23-,24-,28-,29-,31+,32+,33-,34-,35+,36-/m1/s1

InChI Key

NUFCZKSATPHTRO-RPWCKPLOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
C-glycosyl compound
Chromone
1-benzopyran
Benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-glycosyl compound (CHEBI:16954 )
trihydroxyflavone (CHEBI:16954 )
flavones (C01460 )
Flavones and Flavonols (C01460 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301975)

Food

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	1.11	ALOGPS
logP	0.41	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	282.59 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	179.73 m³·mol⁻¹	ChemAxon
Polarizability	72.8 Å³	ChemAxon
Number of Rings	6	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

HMDB0301975

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001701

KNApSAcK ID

Not Available

Chemspider ID

59696234

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101227525

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Isovitexin 7-(6'''-(E)-p-coumaroylglucoside) (CFc000281491)

MOL for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

3D MOL for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

3D SDF for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

3D-SDF for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

PDB for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

3D PDB for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

SMILES for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

INCHI for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

Structure for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))

3D Structure for CFc000281491 (Isovitexin 7-(6'''-(E)-p-coumaroylglucoside))