CHEBI:28819 - naringin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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
Supplier Information eMolecules:31492408, ZINC000003777403
Download Molfile XML SDF
more structures >>
Wikipedia License
Delphinidin (also delphinidine) is an anthocyanidin, a primary plant pigment, and also an antioxidant. Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape variety Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates, and bilberries. Delphinidin, like nearly all other anthocyanidins, is pH-sensitive, i.e. a natural pH indicator, and changes from blue in basic solution to red in acidic solution.
Read full article at Wikipedia
Formula C27H32O14
Net Charge 0
Average Mass 580.53460
Monoisotopic Mass 580.17921
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.
View more via ChEBI Ontology
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 (2S)-flavan-4-one (CHEBI:140377)
naringin (CHEBI:28819) is a 4'-hydroxyflavanones (CHEBI:140331)
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
Manual Xrefs Databases
C00000983 KNApSAcK
C09789 KEGG COMPOUND
HMDB0002927 HMDB
LSM-2038 LINCS
Naringin Wikipedia
NARINGIN MetaCyc
View more database links
Registry Numbers Types Sources
102012 Reaxys Registry Number Reaxys
10236-47-2 CAS Registry Number KEGG COMPOUND
10236-47-2 CAS Registry Number ChemIDplus
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
09 April 2018