CAS 579-13-5|Oligomycin A
Introduction：Basic information about CAS 579-13-5|Oligomycin A, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Oligomycin A | ||
|---|---|---|---|
| CAS Number | 579-13-5 | Molecular Weight | 791.063 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 886.3±65.0 °C at 760 mmHg |
| Molecular Formula | C45H74O11 | Melting Point | 150-151ºC |
| MSDS | ChineseUSA | Flash Point | 252.0±27.8 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | Oligomycin A |
|---|---|
| Synonym | More Synonyms |
Oligomycin A BiologicalActivity
| Description | Oligomycin A, created by Streptomyces, acts as a mitochondrial F0F1-ATPase inhibitor, with a Ki of 1 μM; Oligomycin A shows anti-fungal activity. |
|---|---|
| Related Catalog | Signaling Pathways >>Membrane Transporter/Ion Channel >>ATP SynthaseResearch Areas >>CancerResearch Areas >>InfectionNatural Products >>Others |
| Target | Ki: 1 μM (F0F1-ATPase)[1] |
| In Vitro | Oligomycin A is a mitochondrial F0F1-ATPase inhibitor with a Ki of 1 μM. Oligomycin A shows cytotoxic to the NCI-60 cell lines, with GI50 of 10 nM. Oligomycin A also inhibits the activity of Triton X-100-solubilized ATPase with a Ki of 0.1 μM. Furthermore, Oligomycin A has anti-fungal activity[1]. Oligomycin A (2.4 µM) inhibits the ability of spermatozoa to achieve feasible in vitro capacitation (IVC), and also suppresses progesterone-induced in vitro acrosome exocytosis (IVAE) as well as the concomitant peaks of O2 consumption and ATP levels[2]. |
| Cell Assay | Drug (Oligomycin A, etc.) dilutions are added to monolayer or suspension cells in 96 well plates in triplicate for varying times. MTT is then added to the wells at a final concentration of 0.5 mg/mL. Supernatant is removed after pelleting the reduced MTT crystals. The crystals are fully dissolved in 40 mM HCl in isopropanol. Plates are scanned on a microplate reader at 595 nm[1]. |
| References | [1]. Salomon AR, et al. Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase. Chem Biol. 2001 Jan;8(1):71-80. [2]. Ramió-Lluch L, et al. Oligomycin A-induced inhibition of mitochondrial ATP-synthase activity suppresses boar sperm motility and in vitro capacitation achievement without modifying overall sperm energy levels. Reprod Fertil Dev. 2014;26(6):883-97. |
Chemical & Physical Properties
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 886.3±65.0 °C at 760 mmHg |
| Melting Point | 150-151ºC |
| Molecular Formula | C45H74O11 |
| Molecular Weight | 791.063 |
| Flash Point | 252.0±27.8 °C |
| Exact Mass | 790.523132 |
| PSA | 180.05000 |
| LogP | 6.17 |
| Appearance of Characters | white to off-white |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.543 |
| InChIKey | MNULEGDCPYONBU-AWJDAWNUSA-N |
| SMILES | CCC1C=CC=CCC(C)C(O)C(C)(O)C(=O)C(C)C(O)C(C)C(=O)C(C)C(O)C(C)C=CC(=O)OC2C(C)C(CC1)OC1(CCC(C)C(CC(C)O)O1)C2C |
| Storage condition | −20°C |
| Water Solubility | Soluble in DMSO, ethanol or acetone |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1500 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JACSAT Journal of the American Chemical Society. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1879- Volume(issue)/page/year: 80,6092,1958
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn,T |
| Risk Phrases | 22-68/20/21/22-20/21/22 |
| Safety Phrases | 36/37 |
| RIDADR | UN 2811 |
| WGK Germany | 3 |
| RTECS | RK3325000 |
| Packaging Group | III |
| Hazard Class | 6.1(b) |
| HS Code | 29419090 |
Articles28
More Articles| Modulators of hepatic lipoprotein metabolism identified in a search for small-molecule inducers of tribbles pseudokinase 1 expression. PLoS ONE 10 , e0120295, (2015) Recent genome wide association studies have linked tribbles pseudokinase 1 (TRIB1) to the risk of coronary artery disease (CAD). Based on the observations that increased expression of TRIB1 reduces se... | |
| Functional characterization of CYP107W1 from Streptomyces avermitilis and biosynthesis of macrolide oligomycin A. Arch. Biochem. Biophys. 575 , 1-7, (2015) Streptomyces avermitilis contains 33 cytochrome P450 genes in its genome, many of which play important roles in the biosynthesis process of antimicrobial agents. Here, we characterized the biochemical... | |
| Moles of a Substance per Cell Is a Highly Informative Dosing Metric in Cell Culture. PLoS ONE 10 , e0132572, (2015) The biological consequences upon exposure of cells in culture to a dose of xenobiotic are not only dependent on biological variables, but also the physical aspects of experiments e.g. cell number and ... |
Synonyms
| (1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-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]nonaco |
| (1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-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 |
| Oligomycin A |
| (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 |
| 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'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-, (1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,28R,29S)- |
| MCH 32 |
| MFCD00065705 |
| OLIGOMYCIN,STREPTOMYCES DIASTATOCHROMOGENES |
| EINECS 209-473-3 |
| OLIGOMYCIN A,STREPTOMYCES DIASTATOCHROMOGENES |
