CHEBI:18330 - isovitexin

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ChEBI Name isovitexin
ChEBI ID CHEBI:18330
Definition A C-glycosyl compound that consists of apigenin substituted by a 1,5-anhydro-D-glucitol moiety at position 6.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2771, CHEBI:14482, CHEBI:22806
Supplier Information ChemicalBook:CB8708575, eMolecules:1935879, ZINC000004095704
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Wikipedia License
Isovitexin (or homovitexin, saponaretin) is a flavone, namely the apigenin-6-C-glucoside. In this case, the prefix 'iso' does not imply an isoflavonoid (the position of the B-ring on the C-ring), but the position of the glucoside on the flavone, in comparison to vitexin.
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Formula C21H20O10
Net Charge 0
Average Mass 432.37750
Monoisotopic Mass 432.10565
InChI InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1
InChIKey MYXNWGACZJSMBT-VJXVFPJBSA-N
SMILES OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)c1c(O)cc2oc(cc(=O)c2c1O)-c1ccc(O)cc1
Roles Classification
Biological Role(s): EC 3.2.1.20 (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing isovitexin (CHEBI:18330) has functional parent apigenin (CHEBI:18388)
isovitexin (CHEBI:18330) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
isovitexin (CHEBI:18330) has role metabolite (CHEBI:25212)
isovitexin (CHEBI:18330) is a C-glycosyl compound (CHEBI:20857)
isovitexin (CHEBI:18330) is a trihydroxyflavone (CHEBI:27116)
isovitexin (CHEBI:18330) is conjugate acid of isovitexin-7-olate (CHEBI:58447)
Incoming 2''-O-(β-D-glucosyl)isovitexin (CHEBI:75432) has functional parent isovitexin (CHEBI:18330)
2''-O-(6-feruloylglucosyl)isovitexin (CHEBI:75554) has functional parent isovitexin (CHEBI:18330)
2''-O-(6-sinapoylglucosyl)isovitexin (CHEBI:75428) has functional parent isovitexin (CHEBI:18330)
4'-O-β-glucosyl-7-O-(6-O-sinapoylglucosyl)isovitexin (CHEBI:75564) has functional parent isovitexin (CHEBI:18330)
7-O-(β-D-glucosyl)isovitexin (CHEBI:75439) has functional parent isovitexin (CHEBI:18330)
7-O-(6-sinapoylglucosyl)isovitexin (CHEBI:75413) has functional parent isovitexin (CHEBI:18330)
7-O-[α-L-rhamnosyl-(1→2)-β-D-glucosyl]isovitexin (CHEBI:75438) has functional parent isovitexin (CHEBI:18330)
7-O-[6-(6-methoxycaffeoyl)glucosyl]isovitexin (CHEBI:75420) has functional parent isovitexin (CHEBI:18330)
isovitexin 2''-O-β-D-glucoside (CHEBI:17379) has functional parent isovitexin (CHEBI:18330)
isovitexin 2''-O-arabinoside (CHEBI:75435) has functional parent isovitexin (CHEBI:18330)
isovitexin 2''-O-rhamnoside (CHEBI:142906) has functional parent isovitexin (CHEBI:18330)
isovitexin 7-O-[feruloyl]-glucoside (CHEBI:75368) has functional parent isovitexin (CHEBI:18330)
isovitexin 7-O-[isoferuloyl]-glucoside (CHEBI:75371) has functional parent isovitexin (CHEBI:18330)
isovitexin 8-C-β-glucoside (CHEBI:69814) has functional parent isovitexin (CHEBI:18330)
sinapoyl-isovitexin 2''-O-arabinoside (CHEBI:75386) has functional parent isovitexin (CHEBI:18330)
vicenin-3 (CHEBI:142905) has functional parent isovitexin (CHEBI:18330)
isovitexin-7-olate (CHEBI:58447) is conjugate base of isovitexin (CHEBI:18330)
IUPAC Name
(1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-D-glucitol
Synonyms Sources
6-C-Glucosylapigenin KEGG COMPOUND
6-Glucosylapigenin ChemIDplus
Apigenin 6-C-glucoside KEGG COMPOUND
Apigenin-6-C-glucoside KEGG COMPOUND
beta-D-isovitexin ChEBI
Isovitexin KEGG COMPOUND
Saponaretin KEGG COMPOUND
Manual Xrefs Databases
C00001059 KNApSAcK
C01714 KEGG COMPOUND
Isovitexin Wikipedia
ISOVITEXIN MetaCyc
LMPK12110338 LIPID MAPS
View more database links
Registry Numbers Types Sources
29702-25-8 CAS Registry Number KEGG COMPOUND
38953-85-4 CAS Registry Number KEGG COMPOUND
66651 Reaxys Registry Number Reaxys
Citations
Senol FS, Tuzun CY, Toker G, Orhan IE (2012)
An in vitro perspective to cholinesterase inhibitory and antioxidant activity of five Gentiana species and Gentianella caucasea.
International journal of food sciences and nutrition 63, 802-812 [PubMed:22475010]
[show Abstract]
Ma X, Yan R, Yu S, Lu Y, Li Z, Lu H (2012)
Enzymatic acylation of isoorientin and isovitexin from bamboo-leaf extracts with fatty acids and antiradical activity of the acylated derivatives.
Journal of agricultural and food chemistry 60, 10844-10849 [PubMed:23057589]
[show Abstract]
Choo CY, Sulong NY, Man F, Wong TW (2012)
Vitexin and isovitexin from the Leaves of Ficus deltoidea with in-vivo α-glucosidase inhibition.
Journal of ethnopharmacology 142, 776-781 [PubMed:22683902]
[show Abstract]
Lin CM, Huang ST, Liang YC, Lin MS, Shih CM, Chang YC, Chen TY, Chen CT (2005)
Isovitexin suppresses lipopolysaccharide-mediated inducible nitric oxide synthase through inhibition of NF-kappa B in mouse macrophages.
Planta medica 71, 748-753 [PubMed:16142640]
[show Abstract]
Last Modified
28 July 2014