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CHEBI:67584 - fruticoside A

ChEBI IDCHEBI:67584
ChEBI Namefruticoside A
Stars
DefinitionA 3β-hydroxy steroid that is 4-methylergosta-7,24(28)-dien-3-ol substituted by additional hydroxy groups at positions 2 and 21 (the 2α,3β,4α,5α stereoisomer). It has been isolated from the roots of Breynia fruticosa and exhibits cytotoxic activity against human cancer cell lines.
Last Modified9 January 2014
DownloadsMolfile
FormulaC29H48O3
Net Charge0
Average Mass444.700
Monoisotopic Mass444.36035
SMILES[H][C@@]12CC[C@]([H])([C@H](CO)CCC(=C)C(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC[C@@]2([H])[C@H](C)[C@@H](O)[C@H](O)C[C@]12C
InChIInChI=1S/C29H48O3/c1-17(2)18(3)7-8-20(16-30)23-11-12-24-21-9-10-22-19(4)27(32)26(31)15-29(22,6)25(21)13-14-28(23,24)5/h9,17,19-20,22-27,30-32H,3,7-8,10-16H2,1-2,4-6H3/t19-,20-,22-,23+,24-,25-,26+,27+,28+,29-/m0/s1
InChIKeyOJCFPYLTKWNLCE-CBUQHMQYSA-N
Species of MetaboliteComponentSourceComments
Breynia fruticosa (ncbitaxon:296042) root (BTO:0001188) PubMed (21428418) 90% Methanolic extract of air-dried, crushed roots.
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
fruticoside A (CHEBI:67584) has role antineoplastic agent (CHEBI:35610)
fruticoside A (CHEBI:67584) has role plant metabolite (CHEBI:76924)
fruticoside A (CHEBI:67584) is a 21-hydroxy steroid (CHEBI:35344)
fruticoside A (CHEBI:67584) is a 3β-hydroxy steroid (CHEBI:36836)
fruticoside A (CHEBI:67584) is a triol (CHEBI:27136)
IUPAC Name 
(2α,3β,4α,5α)-4-methylergosta-7,24(28)-diene-2,3,21-triol
Synonym  Source
4α-methyl-2α,3β,21-trihydroxy-5α-ergost-7,24(28)-dieneChEBI
Registry NumbersSources
Reaxys:21553368Reaxys
Citations