| Record Information |
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| Version | 2.0 |
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| Created at | 2024-09-10 20:02:41 UTC |
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| Updated at | 2024-09-10 20:02:41 UTC |
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| NP-MRD ID | NP0334806 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Campest-4-en-3-one |
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| Description | Campest-4-en-3-one 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. In the first step, Campesterol is converted to Campest-4-en-3Beta-ol in presence of enzyme Delta-5-3-Ketosteroid Isomerase. Campest-4-en-3 Beta-ol is converted to Campest-4-en-3-one in presence of enzyme 3-Beta-Hydroxysteroid Dehydrogenase. 3-Oxo-5Alpha-Steroid 4-Dehydrogenase family members (encoded by Det2 in Arabidopsis) catalyze the formation of 5-Alpha-Campestan-3-one. Campest-4-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Campest-4-en-3-one is an intermediate in Brassinolide Biosynthesis pathway. Outside of the human body, campest-4-en-3-one has been detected, but not quantified in, several different foods, such as spelts, kales, japanese walnuts, tree ferns, and oyster mushrooms. This could make campest-4-en-3-one a potential biomarker for the consumption of these foods. The conversion of Campesterol to Campestanol is not a single step, but composed of the biosynthetic sequence of Campesterol 4-en-3Beta-ol ---> 4-en-3-one ---> 3-one ---> Campestanol in Arabidopsis. The conversion of the membrane Sterol Campesterol to BL occurs via a series of reductions, hydroxylations, epimerizations and oxidations that have been extensively studied in several species. In the next step, Campest-4-en-3-one is converted to Campestanol via 5-Alpha-Campestan-3-one. Enzymes that catalyze the conversion from 3-Beta-Hydroxy-Delta,5-6-Steroid to 3-oxo-Delta-4-5 Isomerase have been reported in Bacteria and Mammals. |
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| Structure | CC(C)[C@H](C)CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C InChI=1S/C28H46O/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/h17-20,23-26H,7-16H2,1-6H3/t19-,20-,23?,24?,25?,26?,27+,28-/m1/s1 |
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| Synonyms | | Value | Source |
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| (24R)-Ergost-4-en-3-one | HMDB |
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| Chemical Formula | C28H46O |
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| Average Mass | 398.6642 Da |
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| Monoisotopic Mass | 398.35487 Da |
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| IUPAC Name | (2R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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| Traditional Name | (2R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)[C@H](C)CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C |
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| InChI Identifier | InChI=1S/C28H46O/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/h17-20,23-26H,7-16H2,1-6H3/t19-,20-,23?,24?,25?,26?,27+,28-/m1/s1 |
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| InChI Key | QQIOPZFVTIHASB-PHOXBLGLSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | Not Available |
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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 | Not Available |
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| Substituents | Not Available |
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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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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