| Record Information |
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| Version | 1.0 |
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| Created at | 2020-04-17 18:57:43 UTC |
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| Updated at | 2020-12-07 19:11:24 UTC |
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| CannabisDB ID | CDB004988 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | 5-Dehydroavenasterol |
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| Description | 5-Dehydroavenasterol, also known as 7-dehydroisofucosterol, 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. Thus, 5-dehydroavenasterol is considered to be a sterol lipid molecule. 5-Dehydroavenasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Dehydroavenasterol 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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| (24Z)-24-Ethylcholesta-5,7,24(28)-trien-3beta-ol | HMDB | | (24Z)-24-Ethylcholesta-5,7,24(28)-trien-3β-ol | HMDB | | (24Z)-Stigmasta-5,7,24(28)-trien-3beta-ol | HMDB | | (24Z)-Stigmasta-5,7,24(28)-trien-3β-ol | HMDB | | (3beta,24Z)-Stigmasta-5,7,24(28)-trien-3-ol | HMDB | | (3Β,24Z)-stigmasta-5,7,24(28)-trien-3-ol | HMDB | | 24Z-Ethylidenecholesta-5,7-dien-3beta-ol | HMDB | | 24Z-Ethylidenecholesta-5,7-dien-3β-ol | HMDB | | 7-Dehydroisofucosterol | HMDB | | Stigmasta-5,7-cis-24(28)-trien-3beta-ol | HMDB | | Stigmasta-5,7-cis-24(28)-trien-3β-ol | HMDB | | 5-Dehydroavenasterol | HMDB |
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| Chemical Formula | C29H46O |
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| Average Molecular Weight | 410.69 |
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| Monoisotopic Molecular Weight | 410.3549 |
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| IUPAC Name | (1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol |
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| Traditional Name | (1S,2R,5S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol |
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| CAS Registry Number | 29560-28-9 |
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| SMILES | [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC\C(=C\C)C(C)C |
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| InChI Identifier | InChI=1S/C29H46O/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/h7,10-11,19-20,23,25-27,30H,8-9,12-18H2,1-6H3/b21-7-/t20-,23+,25-,26+,27+,28+,29-/m1/s1 |
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| InChI Key | XPRWWANUPMYKMF-HVEGQNEHSA-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 | - Stigmastane-skeleton
- Triterpenoid
- 3-hydroxy-delta-5-steroid
- 3-hydroxy-delta-7-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-beta-hydroxysteroid
- Delta-7-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Alcohol
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- 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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| Disposition | Route of exposure: Biological location: Source: |
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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 | 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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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | 5-Dehydroavenasterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Dehydroavenasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 5-Dehydroavenasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-0009000000-0f8b3e625297324cedfc | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gbi-3049000000-2747d1c8268b883ffc0f | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a5c-9240000000-e3ed5ab4d8f8f2bdf5b2 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000900000-84eae2c8ad8ccafd7741 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0000900000-3ef7712cbccd003ba144 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1002900000-c36e120707d7a0c2343a | 2021-09-25 | View Spectrum |
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