Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 20:45:27 UTC |
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Update Date | 2022-03-07 02:54:37 UTC |
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HMDB ID | HMDB0035741 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (-)-trans-Isopulegone |
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Description | (-)-trans-Isopulegone, also known as isopulegone, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on (-)-trans-Isopulegone. |
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Structure | InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3 |
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Synonyms | Value | Source |
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1-Methyl-4-isopropenyl-3-cyclohexanone | ChEBI | Isopulegone | ChEBI | (+)-Isopulegone | HMDB | (-)-trans-P-Menth-8-en-3-one | HMDB | (2R-trans)-5-Methyl-2-(1-methylethenyl)-cyclohexanone | HMDB | Pulegone, (S)-isomer | MeSH, HMDB | Pulegone, (R)-isomer | MeSH, HMDB | Pulegone | MeSH, HMDB | cis-Isopulegone | MeSH, HMDB |
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Chemical Formula | C10H16O |
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Average Molecular Weight | 152.2334 |
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Monoisotopic Molecular Weight | 152.120115134 |
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IUPAC Name | 5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one |
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Traditional Name | isopulegone |
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CAS Registry Number | 57129-09-6 |
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SMILES | CC1CCC(C(C)=C)C(=O)C1 |
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InChI Identifier | InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3 |
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InChI Key | RMIANEGNSBUGDJ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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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 | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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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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(-)-trans-Isopulegone,1TMS,isomer #1 | C=C(C)C1=C(O[Si](C)(C)C)CC(C)CC1 | 1389.5 | Semi standard non polar | 33892256 | (-)-trans-Isopulegone,1TMS,isomer #1 | C=C(C)C1=C(O[Si](C)(C)C)CC(C)CC1 | 1349.2 | Standard non polar | 33892256 | (-)-trans-Isopulegone,1TMS,isomer #2 | C=C(C)C1CCC(C)C=C1O[Si](C)(C)C | 1297.8 | Semi standard non polar | 33892256 | (-)-trans-Isopulegone,1TMS,isomer #2 | C=C(C)C1CCC(C)C=C1O[Si](C)(C)C | 1296.5 | Standard non polar | 33892256 | (-)-trans-Isopulegone,1TBDMS,isomer #1 | C=C(C)C1=C(O[Si](C)(C)C(C)(C)C)CC(C)CC1 | 1642.1 | Semi standard non polar | 33892256 | (-)-trans-Isopulegone,1TBDMS,isomer #1 | C=C(C)C1=C(O[Si](C)(C)C(C)(C)C)CC(C)CC1 | 1530.7 | Standard non polar | 33892256 | (-)-trans-Isopulegone,1TBDMS,isomer #2 | C=C(C)C1CCC(C)C=C1O[Si](C)(C)C(C)(C)C | 1513.9 | Semi standard non polar | 33892256 | (-)-trans-Isopulegone,1TBDMS,isomer #2 | C=C(C)C1CCC(C)C=C1O[Si](C)(C)C(C)(C)C | 1454.6 | Standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - (-)-trans-Isopulegone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9200000000-f21ebfb4bb2675e3ee84 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (-)-trans-Isopulegone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 10V, Positive-QTOF | splash10-0udi-0900000000-86c22d1bcbce97c1118d | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 20V, Positive-QTOF | splash10-11or-7900000000-60e1710999312dfb0686 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 40V, Positive-QTOF | splash10-0pvl-9100000000-eb59a6a329c31dd90fd9 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 10V, Negative-QTOF | splash10-0udi-0900000000-a78fe6479a5d6949a074 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 20V, Negative-QTOF | splash10-0udi-0900000000-006545b22bbfa3933fdb | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 40V, Negative-QTOF | splash10-06rx-9700000000-20b227005a182a539522 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 10V, Positive-QTOF | splash10-000i-3900000000-8f6da06f8b0ab70ada65 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 20V, Positive-QTOF | splash10-015c-9200000000-d3bd3bc742e7ae79c7e9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 40V, Positive-QTOF | splash10-00kf-9000000000-eddd98ab96727b2ed663 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 10V, Negative-QTOF | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 20V, Negative-QTOF | splash10-0udi-0900000000-7c68a150979e2bd9e798 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-trans-Isopulegone 40V, Negative-QTOF | splash10-014i-5900000000-6e9f773c05f9e65828bf | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB014470 |
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KNApSAcK ID | C00010948 |
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Chemspider ID | 31884 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 34645 |
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PDB ID | Not Available |
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ChEBI ID | 37046 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1034221 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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