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CHEBI:66627 - niruriside

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:
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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