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CHEBI:31549 - epothilone A

ChEBI IDCHEBI:31549
ChEBI Nameepothilone A
Stars
DefinitionAn epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer).
Secondary ChEBI IDsCHEBI:42387, CHEBI:252957
Last Modified22 September 2015
DownloadsMolfile
FormulaC26H39NO6S
Net Charge0
Average Mass493.666
Monoisotopic Mass493.24981
SMILES[H][C@@]12CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O[C@]([H])(/C(C)=C/c3csc(C)n3)C[C@]1([H])O2
InChIInChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1
InChIKeyHESCAJZNRMSMJG-KKQRBIROSA-N
Roles Classification
Biological Roles:
tubulin modulator  Any substance that interacts with tubulin to inhibit or promote polymerisation of microtubules.
microtubule-stabilising agent  Any substance that interacts with tubulin to promote polymerisation of microtubules.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
epothilone A (CHEBI:31549) has role antineoplastic agent (CHEBI:35610)
epothilone A (CHEBI:31549) has role metabolite (CHEBI:25212)
epothilone A (CHEBI:31549) has role microtubule-stabilising agent (CHEBI:61950)
epothilone A (CHEBI:31549) has role tubulin modulator (CHEBI:60832)
epothilone A (CHEBI:31549) is a epothilone (CHEBI:60831)
epothilone A (CHEBI:31549) is a epoxide (CHEBI:32955)
IUPAC Name 
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
Synonyms  Source
Epothilone AKEGG COMPOUND
EPOTHILONE APDBeChem
(1S,7S,10R,11S,12S,16R)-7-Hydroxy-11-(S)-hydroxy-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dioneChEMBL
(−)-epothilone AChEBI
Epo AChEBI
UniProt Name  Source
epothilone AUniProt
Manual XrefsDatabases
C12153KEGG COMPOUND
EPPDBeChem
LMPK04000040LIPID MAPS
DE4138042Patent
Registry NumbersSources
Reaxys:7555910Reaxys
Citations