CHEBI:66627 - niruriside

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ChEBI Name niruriside
ChEBI ID CHEBI:66627
Definition An O-acyl carbohydrate that consists of β-D-fructofuranosyl β-D-glucopyranoside in which the hydroxy protons are replaced by acetyl and trans-cinnamoyl groups. Isolated from Phyllanthus niruri, it exhibits anti-HIV activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C38H42O17
Net Charge 0
Average Mass 770.72990
Monoisotopic Mass 770.24220
InChI InChI=1S/C38H42O17/c1-22(39)47-20-29-34(50-24(3)41)33(46)35(51-25(4)42)37(52-29)55-38(21-49-23(2)40)36(53-31(44)18-16-27-13-9-6-10-14-27)32(45)28(54-38)19-48-30(43)17-15-26-11-7-5-8-12-26/h5-18,28-29,32-37,45-46H,19-21H2,1-4H3/b17-15+,18-16+/t28-,29-,32-,33+,34-,35-,36+,37+,38+/m1/s1
InChIKey KUZYDHCVYKUFKF-LPLPFJSBSA-N
SMILES CC(=O)OC[C@H]1O[C@@H](O[C@]2(COC(C)=O)O[C@H](COC(=O)\C=C\c3ccccc3)[C@@H](O)[C@@H]2OC(=O)\C=C\c2ccccc2)[C@H](OC(C)=O)[C@@H](O)[C@@H]1OC(C)=O
Metabolite of Species Details
Phyllanthus niruri (NCBI:txid296034) Found in leaf (BTO:0000713). Dried leaves See: PubMed
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.
anti-HIV agent
An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing niruriside (CHEBI:66627) has functional parent trans-cinnamic acid (CHEBI:35697)
niruriside (CHEBI:66627) has role anti-HIV agent (CHEBI:64946)
niruriside (CHEBI:66627) has role metabolite (CHEBI:25212)
niruriside (CHEBI:66627) is a O-acyl carbohydrate (CHEBI:52782)
niruriside (CHEBI:66627) is a acetate ester (CHEBI:47622)
niruriside (CHEBI:66627) is a cinnamate ester (CHEBI:36087)
niruriside (CHEBI:66627) is a disaccharide derivative (CHEBI:63353)
IUPAC Name
1-O-acetyl-3,6-bis-O-[(2E)-3-phenylprop-2-enoyl]-β-D-fructofuranosyl 2,4,6-tri-O-acetyl-β-D-glucopyranoside
Synonyms Sources
alpha-D-Glucopyranoside, 1-O-acetyl-3,6-bis-O-(1-oxo-3-phenyl-2-propenyl)-beta-D-fructofuranosyl, 2,4,6-triacetate, (E,E)- ChemIDplus
β-D-(1-O-acetyl-3,6-O-trans-dicinnamoyl)fructofuranosyl α-D-(2,4,6-O-triacetyl)glucopyranoside ChEBI
Registry Number Type Source
173268-90-1 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
8991954 PubMed citation Europe PMC
Last Modified
16 April 2013