CHEBI:7751 - oligomycin B

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ChEBI Name oligomycin B
ChEBI ID CHEBI:7751
Definition An oligomycin with formula C45H72O12 that is oligomycin A in which the spirocyclic ring bearing the 2-hydroxypropyl substituent has been substituted by an oxo group at the carbon which is directly attached to the spirocentre. It is a nonselective inhibitor of the mitochondrial F1F0 ATP synthase.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C45H72O12
Net Charge 0
Average Mass 805.059
Monoisotopic Mass 804.50238
InChI InChI=1S/C45H72O12/c1-12-33-17-15-13-14-16-25(3)42(52)44(11,54)43(53)31(9)40(51)30(8)39(50)29(7)38(49)24(2)18-21-37(48)55-41-28(6)34(20-19-33)56-45(32(41)10)36(47)22-26(4)35(57-45)23-27(5)46/h13-15,17-18,21,24-35,38,40-42,46,49,51-52,54H,12,16,19-20,22-23H2,1-11H3/b14-13+,17-15+,21-18+/t24-,25+,26-,27+,28+,29-,30-,31-,32-,33-,34-,35-,38+,40+,41+,42-,44+,45+/m0/s1
InChIKey QPRQJOHKNJIMGN-WVUAJZTGSA-N
SMILES CC[C@@H]1CC[C@@H]2O[C@@]3(O[C@@H](C[C@@H](C)O)[C@@H](C)CC3=O)[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).
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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oligomycin B (CHEBI:7751) has role EC 3.6.3.14 (H+-transporting two-sector ATPase) inhibitor (CHEBI:73214)
oligomycin B (CHEBI:7751) is a oligomycin (CHEBI:25675)
oligomycin B (CHEBI:7751) is a pentol (CHEBI:37205)
oligomycin B (CHEBI:7751) is a triketone (CHEBI:140322)
IUPAC Name
(1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27S,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-5',6'-dihydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,3',9,13(4'H)-tetrone
Synonym Source
28-oxo-oligomycin A ChemIDplus
Manual Xrefs Databases
C11312 KEGG COMPOUND
CPD-21957 MetaCyc
EFB PDBeChem
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Registry Numbers Types Sources
11050-94-5 CAS Registry Number KEGG COMPOUND
11050-94-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
24 June 2021