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CHEBI:77692 - peloruside A

ChEBI IDCHEBI:77692
ChEBI Namepeloruside A
Stars
DefinitionA macrolide that is a novel secondary metabolite isolated from a New Zealand marine sponge, Mycale hentscheli.
Last Modified30 September 2015
SubmitterSteve
DownloadsMolfile
FormulaC27H48O11
Net Charge0
Average Mass548.670
Monoisotopic Mass548.31966
SMILESCC[C@@H](/C=C(/C)[C@H]1C[C@H](OC)C[C@@H](O)C(C)(C)[C@]2(O)O[C@H](C[C@H](OC)[C@@H](O)C(=O)O1)C[C@H](OC)[C@@H]2O)CO
InChIInChI=1S/C27H48O11/c1-8-16(14-28)9-15(2)19-10-17(34-5)13-22(29)26(3,4)27(33)24(31)21(36-7)12-18(38-27)11-20(35-6)23(30)25(32)37-19/h9,16-24,28-31,33H,8,10-14H2,1-7H3/b15-9-/t16-,17-,18+,19+,20-,21-,22+,23+,24-,27+/m0/s1
InChIKeyNETARJWZTMGMRM-JRTPPQMASA-N
Roles Classification
Biological Roles:
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
antimitotic  Any compound that inhibits cell division (mitosis).
microtubule-stabilising agent  Any substance that interacts with tubulin to promote polymerisation of microtubules.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
peloruside A (CHEBI:77692) has role antimitotic (CHEBI:64911)
peloruside A (CHEBI:77692) has role antineoplastic agent (CHEBI:35610)
peloruside A (CHEBI:77692) has role marine metabolite (CHEBI:76507)
peloruside A (CHEBI:77692) has role microtubule-stabilising agent (CHEBI:61950)
peloruside A (CHEBI:77692) is a cyclic hemiketal (CHEBI:59780)
peloruside A (CHEBI:77692) is a ether (CHEBI:25698)
peloruside A (CHEBI:77692) is a macrolide (CHEBI:25106)
peloruside A (CHEBI:77692) is a organic heterobicyclic compound (CHEBI:27171)
peloruside A (CHEBI:77692) is a primary alcohol (CHEBI:15734)
peloruside A (CHEBI:77692) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1S,3S,4R,7R,9R,11R,13S,14S,15S)-4,11,13,14-tetrahydroxy-7-[(2Z,4S)-4-(hydroxymethyl)hex-2-en-2-yl]-3,9,15-trimethoxy-12,12-dimethyl-6,17-dioxabicyclo[11.3.1]heptadecan-5-one
Synonym  Source
(−)-peloruside AChEBI
Registry NumbersSources
Reaxys:14282578Reaxys
Citations