CHEBI:31549 - epothilone A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name epothilone A
ChEBI ID CHEBI:31549
Definition An 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).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42387, CHEBI:252957
Supplier Information
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Formula C26H39NO6S
Net Charge 0
Average Mass 493.658
Monoisotopic Mass 493.24981
InChI InChI=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
InChIKey HESCAJZNRMSMJG-KKQRBIROSA-N
SMILES C1[C@](OC(C[C@@H](C(C([C@@H]([C@H]([C@H](CCC[C@@]2([C@]1(O2)[H])[H])C)O)C)=O)(C)C)O)=O)(/C(=C/C=3N=C(SC3)C)/C)[H]
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via epothilone )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(−)-epothilone A ChEBI
(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-dione ChEMBL
Epo A ChEBI
EPOTHILONE A PDBeChem
Epothilone A KEGG COMPOUND
epothilone A UniProt
Manual Xrefs Databases
C12153 KEGG COMPOUND
DE4138042 Patent
EP PDBeChem
LMPK04000040 LIPID MAPS
View more database links
Registry Number Type Source
7555910 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10831849 PubMed citation Europe PMC
11133086 PubMed citation ChEMBL
16134928 PubMed citation ChEMBL
18271516 PubMed citation ChEMBL
9873670 PubMed citation ChEMBL
Last Modified
22 September 2015