CHEBI:7781 - orientin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name orientin
ChEBI ID CHEBI:7781
Definition A C-glycosyl compound that is luteolin substituted by a β-D-glucopyranosyl moiety at position 8.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB7710333, eMolecules:32175083, ZINC000004098560
Download Molfile XML SDF
Wikipedia License
Orientin is a flavone, a chemical flavonoid-like compound. It is the 8-C glucoside of luteolin.
Read full article at Wikipedia
Formula C21H20O11
Net Charge 0
Average Mass 448.37690
Monoisotopic Mass 448.10056
InChI InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1
InChIKey PLAPMLGJVGLZOV-VPRICQMDSA-N
SMILES OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)c1c(O)cc(O)c2c1oc(cc2=O)-c1ccc(O)c(O)c1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): 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 orientin (CHEBI:7781) has functional parent luteolin (CHEBI:15864)
orientin (CHEBI:7781) has role antioxidant (CHEBI:22586)
orientin (CHEBI:7781) has role metabolite (CHEBI:25212)
orientin (CHEBI:7781) is a 3'-hydroxyflavonoid (CHEBI:27741)
orientin (CHEBI:7781) is a C-glycosyl compound (CHEBI:20857)
orientin (CHEBI:7781) is a tetrahydroxyflavone (CHEBI:38684)
Incoming 3''-oxoorientin(1−) (CHEBI:229564) has functional parent orientin (CHEBI:7781)
orientin 2''-O-rhamnoside (CHEBI:142904) has functional parent orientin (CHEBI:7781)
IUPAC Name
2-(3,4-dihydroxyphenyl)-8-β-D-glucopyranosyl-5,7-dihydroxy-4H-chromen-4-one
Synonyms Sources
8-β-D-glucosylluteolin ChEBI
Luteolin 8-C-glucoside
Note: (2007-02-13) Misnomer: IUPAC strongly discourages the use of names based on 'C-glycoside' terminology.
KEGG COMPOUND
Lutexin HMDB
Orientin KEGG COMPOUND
Manual Xrefs Databases
C00001078 KNApSAcK
C10114 KEGG COMPOUND
HMDB0030614 HMDB
LMPK12110470 LIPID MAPS
Orientin Wikipedia
View more database links
Registry Numbers Types Sources
28608-75-5 CAS Registry Number ChemIDplus
69376 Reaxys Registry Number Reaxys
Citations
Simirgiotis MJ, Schmeda-Hirschmann G, Bórquez J, Kennelly EJ (2013)
The Passiflora tripartita (Banana Passion) fruit: a source of bioactive flavonoid C-glycosides isolated by HSCCC and characterized by HPLC–DAD–ESI/MS/MS.
Molecules (Basel, Switzerland) 18, 1672-1692 [PubMed:23358325]
[show Abstract]
Khan RA (2012)
Evaluation of flavonoids and diverse antioxidant activities of Sonchus arvensis.
Chemistry Central journal 6, 126 [PubMed:23107458]
[show Abstract]
Mali VR, Mohan V, Bodhankar SL, Bodhankar SL (2012)
Antihypertensive and cardioprotective effects of the Lagenaria siceraria fruit in NG-nitro-L-arginine methyl ester (L-NAME) induced hypertensive rats.
Pharmaceutical biology 50, 1428-1435 [PubMed:22994444]
[show Abstract]
Kim HJ, Park KJ, Lim JH (2011)
Metabolomic analysis of phenolic compounds in buckwheat (Fagopyrum esculentum M.) sprouts treated with methyl jasmonate.
Journal of agricultural and food chemistry 59, 5707-5713 [PubMed:21417394]
[show Abstract]
Lu N, Sun Y, Zheng X (2011)
Orientin-induced cardioprotection against reperfusion is associated with attenuation of mitochondrial permeability transition.
Planta medica 77, 984-991 [PubMed:21283956]
[show Abstract]
Last Modified
28 July 2014