(5'R,6R,7S,8R,10R,11R,12S,14S,15R,16S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

• ChemBase ID: 156002
• Molecular Formular: C45H74O11
• Molecular Mass: 791.06246
• Monoisotopic Mass: 790.52311319
• SMILES: CCC1CCC2[C@@H](C([C@H](C3(O2)CC[C@H](C(O3)C[C@H](C)O)C)C)OC(=O)/C=C/[C@H]([C@@H]([C@H](C(=O)[C@@H]([C@H]([C@@H](C(=O)[C@@]([C@@H]([C@H](C/C=C/C=C\1)C)O)(C)O)C)O)C)C)O)C)C
• Canonical SMILES: CCC1/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@H]([C@@H](/C=C/C(=O)OC2[C@H](C(CC1)OC1(CC[C@H](C(O1)C[C@@H](O)C)C)[C@@H]2C)C)C)O)C
• 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/t25-,26-,27+,28+,29+,30-,31+,32+,33-,34?,35?,36?,38+,40-,41?,42-,44+,45?/m1/s1
• InChIKey: MNULEGDCPYONBU-YOKYSHDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5'R,6R,7S,8R,10R,11R,12S,14S,15R,16S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione
• IUPAC Traditional name: (5'R,6R,7S,8R,10R,11R,12S,14S,15R,16S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione
• Synonyms: Oligomycin A

Database IDs

• CAS Number: 579-13-5
• EC Number: 209-437-3
• MDL Number: MFCD00065705
• Beilstein Number: 5702132
• PubChem SID: 24886820; 162250140
• PubChem CID: 71312254

CALCULATED PROPERTIES

• Acid pKa: 12.26453
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 7.4476266
• LogD (pH = 7.4): 7.447621
• Log P: 7.4476266
• Molar Refractivity: 219.2278 cm^3
• Polarizability: 86.11735 Å^3
• Polar Surface Area: 180.05 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: RK3328000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C45H74O11

DETAILS

Sigma Aldrich - 75351

Other Notes
Inhibits the growth of Rhodotorula glutinis, Aspergillus niger and other moulds3
Application
Oligomycin is used to inhibit membrane bount mitochondrial ATP synthase. It is used to inhibit sucrose synthesis and 14C translocation in sunflower leaves, to study antibiotic resistance, and to study carotid chemoreceptor responses to O2 and CO2 in the cat 1,2.
Biochem/physiol Actions
Oligomycin inhibits membrane bound mitochondrial ATP synthase (ATPase), proton channel (pump, FO subunit) blockers thereby inhibiting oxidative phosphorylation and the electron transport chain.