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CHEBI:7751 - oligomycin B

ChEBI IDCHEBI:7751
ChEBI Nameoligomycin B
Stars
DefinitionAn 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.
Last Modified24 June 2021
DownloadsMolfile
FormulaC45H72O12
Net Charge0
Average Mass805.059
Monoisotopic Mass804.50238
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(O[C@@H](C[C@@H](C)O)[C@@H](C)CC1=O)[C@H]2C
InChIInChI=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
InChIKeyQPRQJOHKNJIMGN-WVUAJZTGSA-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).
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.
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.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
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 AChemIDplus
Manual XrefsDatabases
C11312KEGG COMPOUND
EFBPDBeChem
CPD-21957MetaCyc
Registry NumbersSources
CAS:11050-94-5KEGG COMPOUND
CAS:11050-94-5ChemIDplus
Citations