| Record Information |
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| Version | 1.0 |
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| Created at | 2020-04-17 19:34:00 UTC |
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| Updated at | 2020-12-07 19:12:00 UTC |
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| CannabisDB ID | CDB005346 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | 5a-Cholesta-7,24-dien-3b-ol |
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| Description | PC(20:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(20:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one eicosanoyl chain to the C-1 atom, and one 5Z,8Z,11Z,14Z-eicosatetraenoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate. 5a-Cholesta-7,24-dien-3b-ol is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-Arachidoyl-2-arachidonoyl-sn-glycero-3-phosphocholine | ChEBI | | 1-C20:0-2-C20:4(Omega-6)-phosphatidylcholine | ChEBI | | 1-Eicosanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine | ChEBI | | 1-Eicosanoyl-2-arachidonoyl-sn-glycero-3-phosphocholine | ChEBI | | 1-Icosanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholine | ChEBI | | PC(20:0/20:4) | ChEBI | | PC(20:0/20:4omega6) | ChEBI | | PC(40:4) | ChEBI | | Phosphatidylcholine(20:0/20:4) | ChEBI | | Phosphatidylcholine(20:0/20:4omega6) | ChEBI | | Phosphatidylcholine(40:4) | ChEBI | | 1-Arachidonyl-2-arachidonoyl-sn-glycero-3-phosphocholine | HMDB | | GPCho(20:0/20:4) | HMDB | | Lecithin | HMDB | | GPCho(40:4) | HMDB | | 1-Eicosanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine | HMDB | | 5 alpha-Cholesta-7,24-dien-3beta-ol | HMDB | | 5alpha-Cholesta-7,24-dien-3beta-ol | HMDB | | 5 alpha-Cholesta-7,24-dien-3 beta-ol | MeSH, HMDB | | Cholesta-7,24-dien-3-ol | MeSH, HMDB | | Cholesta-7,24-dien-3-ol, (3beta)-isomer | MeSH, HMDB |
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| Chemical Formula | C27H44O |
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| Average Molecular Weight | 384.64 |
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| Monoisotopic Molecular Weight | 384.3392 |
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| IUPAC Name | (2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol |
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| Traditional Name | (2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol |
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| CAS Registry Number | 651-54-7 |
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| SMILES | [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)C3CC[C@]12C |
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| InChI Identifier | InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,10,19-21,23-25,28H,6,8-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25?,26+,27-/m1/s1 |
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| InChI Key | PKEPPDGGTSZLBL-FZAJRYLSSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Glycerophospholipids |
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| Sub Class | Glycerophosphocholines |
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| Direct Parent | Phosphatidylcholines |
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| Alternative Parents | |
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| Substituents | - Diacylglycero-3-phosphocholine
- Phosphocholine
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Quaternary ammonium salt
- Tetraalkylammonium salt
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Amine
- Organic salt
- Hydrocarbon derivative
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Industrial application: Biological role: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 147 - 151 °C | 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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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | 5a-Cholesta-7,24-dien-3b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0aor-1019000000-626e97645b632a1ff077 | Spectrum | | Predicted GC-MS | 5a-Cholesta-7,24-dien-3b-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002f-3005900000-d8ed9d20e09e9fa8cc7d | Spectrum |
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