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CHEBI:66168 - (1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol

ChEBI IDCHEBI:66168
ChEBI Name(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol
Stars
ASCII Name(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol
DefinitionA germacrane sesquiterpenoid that is 4,5-epoxygermacra-9Z-ene substituted by hydroxy groups at positions 1, 2 and 6. Isolated from Santolina insularis, it exhibits cytotoxicity against human colon carcinoma cell line.
Last Modified25 September 2013
DownloadsMolfile
FormulaC15H26O4
Net Charge0
Average Mass270.369
Monoisotopic Mass270.18311
SMILES[H][C@@]12O[C@@]1(C)C[C@@H](O)[C@H](O)/C(C)=C\C[C@@H](C(C)C)[C@H]2O
InChIInChI=1S/C15H26O4/c1-8(2)10-6-5-9(3)12(17)11(16)7-15(4)14(19-15)13(10)18/h5,8,10-14,16-18H,6-7H2,1-4H3/b9-5-/t10-,11+,12+,13+,14-,15-/m0/s1
InChIKeyUOUMJKKOPWRYPB-QBCLFKMJSA-N
Species of MetaboliteComponentSourceComments
Santolina insularis (ncbitaxon:765941) aerial part (BTO:0001658) PubMed (15974607)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) has role antineoplastic agent (CHEBI:35610)
(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) has role metabolite (CHEBI:25212)
(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) is a epoxide (CHEBI:32955)
(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) is a germacrane sesquiterpenoid (CHEBI:68588)
(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) is a triol (CHEBI:27136)
IUPAC Name 
(1S,2R,3S,5Z,7R,8R,10S)-6,10-dimethyl-3-(propan-2-yl)-11-oxabicyclo[8.1.0]undec-5-ene-2,7,8-triol
Registry NumbersSources
Reaxys:15769284Reaxys
Citations