Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:48:31 UTC |
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Updated at | 2022-03-10 22:17:42 UTC |
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NP-MRD ID | NP0044315 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5alpha-Campestan-3-one |
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Description | 5Alpha-campestan-3-one, also known as 3-dehydro-campestanol or methylcholestanone, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 5alpha-campestan-3-one is considered to be a sterol lipid molecule. 5Alpha-campestan-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5Alpha-Campestan-3-one is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-21,23-26H,7-17H2,1-6H3/t19-,20-,21+,23+,24-,25+,26+,27+,28-/m1/s1 |
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Synonyms | Value | Source |
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(24R)-24-Methyl-5alpha-cholestan-3-one | ChEBI | (24R)-5alpha-Ergostan-3-one | ChEBI | 3-Dehydro-campestanol | ChEBI | Campestan-3-one | ChEBI | Methylcholestanone | ChEBI | (24R)-24-Methyl-5a-cholestan-3-one | Generator | (24R)-24-Methyl-5α-cholestan-3-one | Generator | (24R)-5a-Ergostan-3-one | Generator | (24R)-5Α-ergostan-3-one | Generator | 5a-Campestan-3-one | Generator | 5Α-campestan-3-one | Generator | (5alpha)-Campestan-3-one | HMDB | (5alpha,24R)-Ergostan-3-one | HMDB | (5α)-Campestan-3-one | HMDB | (5α,24R)-Ergostan-3-one | HMDB | 5alpha-Campestan-3-one | HMDB | Ostreastanone | HMDB |
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Chemical Formula | C28H48O |
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Average Mass | 400.6910 Da |
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Monoisotopic Mass | 400.37052 Da |
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IUPAC Name | (1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one |
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Traditional Name | (1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one |
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CAS Registry Number | 27212-88-0 |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C |
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InChI Identifier | InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-21,23-26H,7-17H2,1-6H3/t19-,20-,21+,23+,24-,25+,26+,27+,28-/m1/s1 |
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InChI Key | DDJMOMHMVFXEQF-JBQSTXLYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Ergostane steroids |
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Direct Parent | Ergosterols and derivatives |
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Alternative Parents | |
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Substituents | - Ergosterol-skeleton
- 3-oxo-5-alpha-steroid
- Oxosteroid
- 3-oxosteroid
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Kyselka J, Honzikova T, Vachalova T, Jiraskova T, Alishevich K, Rottnerova Z, Brychova V, Bercikova M, Hradkova I, Filip V: Formation of 5alpha-Sitostan-3-one, 5alpha-Campestan-3-one, and Steroidal Hydrocarbons in Edible Oils during Catalytic Hydrogenation. J Agric Food Chem. 2019 Sep 4;67(35):9916-9925. doi: 10.1021/acs.jafc.9b03054. Epub 2019 Aug 22. [PubMed:31398025 ]
- Nomura T, Jager CE, Kitasaka Y, Takeuchi K, Fukami M, Yoneyama K, Matsushita Y, Nyunoya H, Takatsuto S, Fujioka S, Smith JJ, Kerckhoffs LH, Reid JB, Yokota T: Brassinosteroid deficiency due to truncated steroid 5alpha-reductase causes dwarfism in the lk mutant of pea. Plant Physiol. 2004 Aug;135(4):2220-9. doi: 10.1104/pp.104.043786. Epub 2004 Jul 30. [PubMed:15286289 ]
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