CHEBI:28285 - oligomycin A

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ChEBI Name oligomycin A
ChEBI ID CHEBI:28285
Definition An oligomycin with formula C45H74011. An inhibitor of mitochondrial F1FO ATP synthase that induces apoptosis in a variety of cell types and exhibits antifungal, antitumour, and nematicidal activities, but its clinical application has been limited by poor solubility in water and other biocompatible solvents.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:25674, CHEBI:7750
Supplier Information
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Formula C45H74O11
Net Charge 0
Average Mass 791.076
Monoisotopic Mass 790.52311
InChI InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m0/s1
InChIKey MNULEGDCPYONBU-AWJDAWNUSA-N
SMILES CC[C@@H]1CC[C@@H]2O[C@]3(CC[C@H](C)[C@H](C[C@@H](C)O)O3)[C@@H](C)[C@H](OC(=O)\C=C\[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@](C)(O)[C@@H](O)[C@H](C)C\C=C\C=C\1)[C@@H]2C
Roles Classification
Biological Role(s): EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of H+-transporting two-sector ATPase inhibitor (EC 3.6.3.14).
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via oligomycin )
(via macrolide antibiotic )
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via oligomycin )
ATP synthase inhibitor
A mitochondrial respiratory-chain inhibitor that interferes with the action of ATP synthase.
(via oligomycin )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
nematicide
A substance used to destroy pests of the phylum Nematoda (roundworms).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oligomycin A (CHEBI:28285) has role antineoplastic agent (CHEBI:35610)
oligomycin A (CHEBI:28285) has role EC 3.6.3.14 (H+-transporting two-sector ATPase) inhibitor (CHEBI:73214)
oligomycin A (CHEBI:28285) has role nematicide (CHEBI:25491)
oligomycin A (CHEBI:28285) is a antibiotic antifungal agent (CHEBI:86478)
oligomycin A (CHEBI:28285) is a diketone (CHEBI:46640)
oligomycin A (CHEBI:28285) is a oligomycin (CHEBI:25675)
oligomycin A (CHEBI:28285) is a pentol (CHEBI:37205)
IUPAC Name
(1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione
Synonyms Sources
Oligomycin A ChemIDplus
RP-32705 ChemIDplus
Manual Xrefs Databases
C11311 KEGG COMPOUND
CPD-21956 MetaCyc
EFO PDBeChem
LSM-43230 LINCS
LSM-43272 LINCS
LSM-43347 LINCS
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Registry Numbers Types Sources
5702132 Reaxys Registry Number Reaxys
579-13-5 CAS Registry Number KEGG COMPOUND
579-13-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22869738 PubMed citation Europe PMC
233519 PubMed citation Europe PMC
24084683 PubMed citation Europe PMC
25849761 PubMed citation Europe PMC
28420869 PubMed citation Europe PMC
29650704 PubMed citation Europe PMC
Last Modified
24 June 2021