CHEBI:28819 - naringin

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ChEBI Name naringin
ChEBI ID CHEBI:28819
Definition A disaccharide derivative that is (S)-naringenin substituted by a 2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:545774, CHEBI:25486, CHEBI:566122, CHEBI:7485
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Formula C27H32O14
Net Charge 0
Average Mass 580.53460
Monoisotopic Mass 580.179
InChI InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
InChIKey DFPMSGMNTNDNHN-ZPHOTFPESA-N
SMILES C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2Oc2cc(O)c3C(=O)C[C@H](Oc3c2)c2ccc(O)cc2)[C@H](O)[C@H](O)[C@H]1O
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
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ChEBI Ontology
Outgoing naringin (CHEBI:28819) has functional parent (S)-naringenin (CHEBI:17846)
naringin (CHEBI:28819) has role anti-inflammatory agent (CHEBI:67079)
naringin (CHEBI:28819) has role antineoplastic agent (CHEBI:35610)
naringin (CHEBI:28819) has role metabolite (CHEBI:25212)
naringin (CHEBI:28819) is a dihydroxyflavanone (CHEBI:38749)
naringin (CHEBI:28819) is a disaccharide derivative (CHEBI:63353)
naringin (CHEBI:28819) is a neohesperidoside (CHEBI:25495)
IUPAC Name
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside
Synonyms Sources
Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside] KEGG COMPOUND
Naringenin 7-O-α-L-rhamnosyl-(1→2)-β-D-glucoside ChEBI
Naringenin 7-O-neohesperidoside KEGG COMPOUND
Naringin KEGG COMPOUND
Naringoside ChemIDplus
Database Links Databases
C00000983 KNApSAcK
C09789 KEGG COMPOUND
HMDB0002927 HMDB
LSM-2038 LINCS
Naringin Wikipedia
NARINGIN MetaCyc
View more database links
Registry Numbers Types Sources
102012 Beilstein Registry Number Beilstein
102012 Reaxys Registry Number Reaxys
10236-47-2 CAS Registry Number KEGG COMPOUND
10236-47-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21636685 PubMed citation Europe PMC
22847135 PubMed citation Europe PMC
22965302 PubMed citation Europe PMC
22985397 PubMed citation Europe PMC
23111634 PubMed citation Europe PMC
Last Modified
24 February 2016