Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2022-03-07 02:51:53 UTC |
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HMDB ID | HMDB0015168 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cerulenin |
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Description | Cerulenin belongs to the class of organic compounds known as oxirane carboxylic acids and derivatives. Oxirane carboxylic acids and derivatives are compounds containing an oxirane ring bearing a carboxylic acid group (or a derivative thereof). At an intraperitoneal dose of 30 milligrams per kilogram, it has been shown to inhibit feeding and induce dramatic weight loss in mice by a mechanism similar to, but independent or downstream of, leptin signaling. Cerulenin is a drug which is used for use as a biochemical tool, cerulenin is shown to cause dramatic weight loss in animals. Cerulenin is an antifungal antibiotic that inhibits fatty acid and steroid biosynthesis. Cerulenin is an extremely weak basic (essentially neutral) compound (based on its pKa). Cerulenin is a potentially toxic compound. Inhibition involves covalent thioacylation that permanently inactivates the enzymes. These two behaviors may increase the availability of energy in the form of ATP, perhaps sensed by AMPK, in the hypothalamus. It is found naturally in the industrial strain Cephalosporium caerulens (Sarocladium oryzae, the sheath rot pathogen of rice). In sterol synthesis, cerulenin inhibits HMG-CoA synthetase activity. But in general conclusion, cerulenin has inhibitory effects on sterol synthesis. It also has the related activity of stimulating fatty acid oxidation through the activation of CPT1, another enzyme normally inhibited by malonyl-CoA. Cerulenin causes a dose-dependent decrease in HER2/neu protein levels in breast cancer cells, from 14% at 1.25 to 78% at 10 milligrams per liter, and targeting of fatty acid synthase by related drugs has been suggested as a possible treatment. In fatty acid synthesis, it has been reported to bind in equimolar ratio to b-keto-acyl-ACP synthase, one of the seven moieties of fatty acid synthase, blocking the interaction of malonyl-CoA. It was also reported that cerulenin specifically inhibited fatty acid biosynthesis in Saccharomyces cerevisiae without having an effect on sterol formation. |
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Structure | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/t10-,11-/m1/s1 |
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Synonyms | Value | Source |
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(2R,3S)-3-(Nona-4,7-dienoyl)oxirane-2-carboximidate | HMDB |
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Chemical Formula | C12H17NO3 |
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Average Molecular Weight | 223.2683 |
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Monoisotopic Molecular Weight | 223.120843415 |
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IUPAC Name | (2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide |
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Traditional Name | cerulenin |
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CAS Registry Number | 17397-89-6 |
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SMILES | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(N)=O |
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InChI Identifier | InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/t10-,11-/m1/s1 |
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InChI Key | GVEZIHKRYBHEFX-GHMZBOCLSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as oxirane carboxylic acids and derivatives. Oxirane carboxylic acids and derivatives are compounds containing an oxirane ring bearing a carboxylic acid group (or a derivative thereof). |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Epoxides |
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Sub Class | Oxirane carboxylic acids and derivatives |
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Direct Parent | Oxirane carboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Oxirane carboxylic acid or derivatives
- Monosaccharide
- Carboxamide group
- Ketone
- Primary carboxylic acid amide
- Carboxylic acid derivative
- Dialkyl ether
- Ether
- Oxacycle
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 93.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1.6 g/L | Not Available | LogP | 1.2 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Cerulenin,1TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(N)=O | 1923.7 | Semi standard non polar | 33892256 | Cerulenin,1TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(N)=O | 1835.2 | Standard non polar | 33892256 | Cerulenin,1TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(N)=O | 2847.3 | Standard polar | 33892256 | Cerulenin,1TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(N)=O | 1946.4 | Semi standard non polar | 33892256 | Cerulenin,1TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(N)=O | 1767.1 | Standard non polar | 33892256 | Cerulenin,1TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(N)=O | 2860.6 | Standard polar | 33892256 | Cerulenin,1TMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C | 1874.0 | Semi standard non polar | 33892256 | Cerulenin,1TMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C | 1886.5 | Standard non polar | 33892256 | Cerulenin,1TMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C | 2553.9 | Standard polar | 33892256 | Cerulenin,2TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C | 1955.6 | Semi standard non polar | 33892256 | Cerulenin,2TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C | 2022.9 | Standard non polar | 33892256 | Cerulenin,2TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C | 2363.5 | Standard polar | 33892256 | Cerulenin,2TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C | 2002.0 | Semi standard non polar | 33892256 | Cerulenin,2TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C | 1992.4 | Standard non polar | 33892256 | Cerulenin,2TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C | 2417.1 | Standard polar | 33892256 | Cerulenin,2TMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2006.2 | Semi standard non polar | 33892256 | Cerulenin,2TMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2066.1 | Standard non polar | 33892256 | Cerulenin,2TMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2318.7 | Standard polar | 33892256 | Cerulenin,3TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2058.0 | Semi standard non polar | 33892256 | Cerulenin,3TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2138.5 | Standard non polar | 33892256 | Cerulenin,3TMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2164.2 | Standard polar | 33892256 | Cerulenin,3TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2096.7 | Semi standard non polar | 33892256 | Cerulenin,3TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2142.4 | Standard non polar | 33892256 | Cerulenin,3TMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2227.3 | Standard polar | 33892256 | Cerulenin,1TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(N)=O | 2166.3 | Semi standard non polar | 33892256 | Cerulenin,1TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(N)=O | 2042.9 | Standard non polar | 33892256 | Cerulenin,1TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(N)=O | 2905.4 | Standard polar | 33892256 | Cerulenin,1TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(N)=O | 2184.3 | Semi standard non polar | 33892256 | Cerulenin,1TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(N)=O | 1958.6 | Standard non polar | 33892256 | Cerulenin,1TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(N)=O | 2919.1 | Standard polar | 33892256 | Cerulenin,1TBDMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2092.9 | Semi standard non polar | 33892256 | Cerulenin,1TBDMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2101.5 | Standard non polar | 33892256 | Cerulenin,1TBDMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2587.9 | Standard polar | 33892256 | Cerulenin,2TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2392.0 | Semi standard non polar | 33892256 | Cerulenin,2TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2393.2 | Standard non polar | 33892256 | Cerulenin,2TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2517.7 | Standard polar | 33892256 | Cerulenin,2TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2435.3 | Semi standard non polar | 33892256 | Cerulenin,2TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2346.6 | Standard non polar | 33892256 | Cerulenin,2TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N[Si](C)(C)C(C)(C)C | 2553.3 | Standard polar | 33892256 | Cerulenin,2TBDMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2439.2 | Semi standard non polar | 33892256 | Cerulenin,2TBDMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2464.9 | Standard non polar | 33892256 | Cerulenin,2TBDMS,isomer #3 | CC=CCC=CCCC(=O)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2435.2 | Standard polar | 33892256 | Cerulenin,3TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2700.4 | Semi standard non polar | 33892256 | Cerulenin,3TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2639.1 | Standard non polar | 33892256 | Cerulenin,3TBDMS,isomer #1 | CC=CCC=CCCC(O[Si](C)(C)C(C)(C)C)=C1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2400.1 | Standard polar | 33892256 | Cerulenin,3TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2734.5 | Semi standard non polar | 33892256 | Cerulenin,3TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2676.0 | Standard non polar | 33892256 | Cerulenin,3TBDMS,isomer #2 | CC=CCC=CCC=C(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2419.8 | Standard polar | 33892256 |
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