CAS 579-13-5: oligomycin A

Description:Oligomycin A is a macrolide antibiotic that is primarily known for its role as an inhibitor of ATP synthase, an essential enzyme in the process of oxidative phosphorylation in mitochondria. It is produced by the fermentation of certain Streptomyces species. Oligomycin A exhibits a complex structure characterized by a large lactone ring and multiple hydroxyl and methoxy groups, contributing to its biological activity. This compound is particularly significant in biochemical research, as it is used to study mitochondrial function and energy metabolism. Its mechanism of action involves binding to the F0 subunit of ATP synthase, effectively blocking proton translocation and preventing ATP production, which can lead to cell death in certain contexts. Oligomycin A is also noted for its potential applications in cancer research, as it can induce apoptosis in cancer cells by disrupting their energy supply. However, its use is primarily confined to laboratory settings due to its potent effects and potential toxicity.

Formula:C₄₅H₇₄O₁₁

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/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

InChI key:InChIKey=MNULEGDCPYONBU-AWJDAWNUSA-N

SMILES:O=C1OC2C(C)C(OC3(OC(CC(O)C)C(C)CC3)C2C)CCC(C=CC=CCC(C)C(O)C(O)(C(=O)C(C)C(O)C(C(=O)C(C)C(O)C(C=C1)C)C)C)CC

Synonyms:
(1R,2′R,4E,5′S,6S,6′S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,28S,29R)-22-Ethyl-3′,4′,5′,6′-tetrahydro-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′-[2H]pyran]-3,9,13-trione
(1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2S)-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
(1S,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,22S,25R,27S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2S)-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
Brn 5702132
Mch 32
Rp-32705
Spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2′-[2H]pyran]-3,9,13-trione, 22-ethyl-3′,4′,5′,6′-tetrahydro-7,11,14,15-tetrahydroxy-6′-[(2R)-2-hydroxypropyl]-5′,6,8,10,12,14,16,28,29-nonamethyl-, (1R,2′R,4E,5′S,6S,6′S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,28S,29R)-
Spiro[2,26-dioxabicyclo[23.3.1]nonacosane-27,2′-[2H]pyran], oligomycin A deriv.

Found 8 products.

Product data	Purity	Price range	Estimated delivery
Spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,9,13-trione,22-ethyl-3',4',5',6'-tetrahydro-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-,(1R,2'R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,28S,29R)- REF: IN-DA00E9LRCAS: 579-13-5	99%	To inquire	Fri 02 May 25
Oligomycin A REF: 54-BUP09168CAS: 579-13-5	≥98%	826.00 €~2,453.00 €	Fri 02 May 25
Oligomycin A REF: TM-T6323CAS: 579-13-5	99.84% - 99.89%	To inquire	Thu 08 May 25
Oligomycin A fromStreptomyces diastatochromogenes REF: 54-BIO1003CAS: 579-13-5	By hplc: 98.68% (Typical Value in Batch COA)	134.00 €~6,100.00 €	Thu 08 May 25
Oligomycin A REF: 7W-GA0390CAS: 579-13-5	(HPLC) ≥ 99.0%	243.00 €	Thu 08 May 25
Oligomycin A, Streptomyces diastatochromogenes. REF: 10-M02220CAS: 579-13-5	- - -	To inquire	Tue 13 May 25
Oligomycin A REF: TR-O532970CAS: 579-13-5	- - -	146.00 €~317.00 €	Tue 13 May 25
Oligomycin A REF: 3D-AO65694CAS: 579-13-5	Min. 95%	289.00 €~1,149.00 €	Thu 12 Jun 25