Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:29:12 UTC |
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Updated at | 2020-11-18 16:35:00 UTC |
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CannabisDB ID | CDB000290 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Stigmast-4-en-3-one |
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Description | Stigmast-4-en-3-one belongs to the class of organic compounds known as stigmastanes and derivatives. These are steroid-like molecules with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 and a trans double bond in position C22. Stigmast-4-en-3-one is a naturally occurring phytosterol found in plants. Phytosterols consist of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or presence or absence of a double bond. They play a similar role to cholesterol in stabilizing membrane lipids in plants. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. In humans the intake of naturally occurring phytosterols ranges between ~200–300 mg/day depending on eating habits (PMID: 28702423 ). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423 ). They may also have a role in cancer prevention and treatment (PMID: 26086253 ). Stigmast-4-en-3-one is one of several phytosterols found in cannabis plants (PMID: 6991645 ). |
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Structure | |
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Synonyms | Value | Source |
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Stigmast-4-en-3-one | PhytoBank | (24R)-24-Ethylcholest-4-en-3-one | PhytoBank | (24R)-Stigmast-4-en-3-one | PhytoBank | 4-En-3-stigmastone | PhytoBank | Sitostenone | PhytoBank | delta4-Sitosterol-3-one | PhytoBank | Δ4-Sitosterol-3-one | PhytoBank | delta4-Stigmasten-3-one | PhytoBank | Δ4-Stigmasten-3-one | PhytoBank | beta-Rosasterol oxide | PhytoBank | β-Rosasterol oxide | PhytoBank | beta-Sitost-4-en-3-one | PhytoBank | β-Sitost-4-en-3-one | PhytoBank | beta-Sitostenone | PhytoBank |
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Chemical Formula | C29H48O |
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Average Molecular Weight | 412.7 |
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Monoisotopic Molecular Weight | 412.3705 |
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IUPAC Name | (1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-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 | (1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-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 | 67392-96-5 |
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SMILES | CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C |
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InChI Identifier | InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1 |
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InChI Key | RUVUHIUYGJBLGI-XJZKHKOHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. |
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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 | Stigmastanes and derivatives |
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Direct Parent | Stigmastanes and derivatives |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Stigmastane-skeleton
- Oxosteroid
- 3-oxosteroid
- 3-oxo-delta-4-steroid
- Delta-4-steroid
- Cyclohexenone
- 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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Ontology |
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Not Available | Physical Properties |
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State | Solid |
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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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