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CHEBI:66627 - niruriside

Default Structure
ChEBI IDCHEBI:66627
ChEBI Nameniruriside
Stars
DefinitionAn 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.
Last Modified16 April 2013
DownloadsMolfile
FormulaC38H42O17
Net Charge0
Average Mass770.737
Monoisotopic Mass770.24220
SMILESCC(=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
InChIInChI=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
InChIKeyKUZYDHCVYKUFKF-LPLPFJSBSA-N
Species of MetaboliteComponentSourceComments
Phyllanthus niruri (ncbitaxon:296034) leaf (BTO:0000713) PubMed (8991954) Dried leaves
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
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)glucopyranosideChEBI
Registry NumbersSources
CAS:173268-90-1ChemIDplus
Citations