CHEBI:77692 - peloruside A

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ChEBI Name peloruside A
ChEBI ID CHEBI:77692
Definition A macrolide that is a novel secondary metabolite isolated from a New Zealand marine sponge, Mycale hentscheli.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000014127890
Download Molfile XML SDF
Formula C27H48O11
Net Charge 0
Average Mass 548.66340
Monoisotopic Mass 548.31966
InChI InChI=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
InChIKey NETARJWZTMGMRM-JRTPPQMASA-N
SMILES CC[C@H](CO)\C=C(\C)[C@H]1C[C@@H](C[C@@H](O)C(C)(C)[C@]2(O)O[C@@H](C[C@H](OC)[C@@H]2O)C[C@H](OC)[C@@H](O)C(=O)O1)OC
Roles Classification
Biological Role(s): 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(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 A ChEBI
Registry Number Type Source
14282578 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12067973 PubMed citation Europe PMC
20107863 PubMed citation Europe PMC
20862516 PubMed citation Europe PMC
21926482 PubMed citation Europe PMC
22180309 PubMed citation Europe PMC
22326528 PubMed citation Europe PMC
22584948 PubMed citation Europe PMC
22594877 PubMed citation Europe PMC
24056987 PubMed citation Europe PMC
24060965 PubMed citation Europe PMC
24156744 PubMed citation Europe PMC
24245693 PubMed citation Europe PMC
24470331 PubMed citation Europe PMC
Last Modified
30 September 2015