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CHEBI:28285 - oligomycin A

ChEBI IDCHEBI:28285
ChEBI Nameoligomycin A
Stars
DefinitionAn 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.
Secondary ChEBI IDsCHEBI:7750, CHEBI:25674
Last Modified24 June 2021
DownloadsMolfile
FormulaC45H74O11
Net Charge0
Average Mass791.076
Monoisotopic Mass790.52311
SMILESCC[C@H]1/C=C/C=C/C[C@@H](C)[C@H](O)[C@@](C)(O)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)/C=C/C(=O)O[C@@H]2[C@H](C)[C@H](CC1)O[C@]1(CC[C@H](C)[C@H](C[C@@H](C)O)O1)[C@H]2C
InChIInChI=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
InChIKeyMNULEGDCPYONBU-AWJDAWNUSA-N
Roles Classification
Biological Roles:
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).
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ATP synthase inhibitor  A mitochondrial respiratory-chain inhibitor that interferes with the action of ATP synthase.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
nematicide  A substance used to destroy pests of the phylum Nematoda (roundworms).
ChEBI Ontology
Outgoing Relation(s)
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  Source
RP-32705ChemIDplus
Oligomycin AChemIDplus
Manual XrefsDatabases
C11311KEGG COMPOUND
LSM-43347LINCS
LSM-43272LINCS
LSM-43230LINCS
CPD-21956MetaCyc
EFOPDBeChem
Registry NumbersSources
Reaxys:5702132Reaxys
CAS:579-13-5KEGG COMPOUND
CAS:579-13-5ChemIDplus
Citations