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Oligomycin B

CAT: 0013-GTR19205256-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19205256-01Size:1 mg
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Description
Oligomycin B is a marine-derived Streptomyces antibiotic that acts as a specific inhibitor of eukaryotic ATP synthase. This inhibition disrupts cellular energy production, leading to the induction of apoptosis, making it a valuable tool for studying mitochondrial function, bioenergetics, and cell death mechanisms in both in vitro and in vivo research models.
CAS Number
11050-94-5
Field of Research
Cell Biology, Infectious Disease & Virology, Pharmacology & Drug Discovery
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
Molecular Formula
C45H72O12
Molecular Weight
805.05
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

Oligomycin B

Oligomycin B is 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. It has a role as an EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor. It is a triketone, an oligomycin and a pentol.

CAS Number11050-94-5
PubChem CID76958645
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-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,3',9,13-tetrone
Molecular FormulaC45H72O12
Molecular Weight805.0
XLogP6.1
Topological Polar Surface Area197
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count3
Heavy Atom Count57
Formal Charge0
Complexity1470
SMILES
CC[C@@H]\1CC[C@H]2[C@H]([C@H]([C@@H]([C@]3(O2)C(=O)C[C@@H]([C@@H](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=C1)C)O)(C)O)C)O)C)C)O)C)C
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
Chemical Structure
2D Structure
2D structure of Oligomycin B
CAS: 11050-94-5
CID: 76958645
Formula: C45H72O12
MW: 805.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight805.0
XLogP36.1
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count3
Exact Mass804.50237773
Monoisotopic Mass804.50237773
Topological Polar Surface Area197 Ų
Heavy Atom Count57
Formal Charge0
Complexity1470
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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