| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:01:23 UTC |
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| Update Date | 2020-05-21 16:27:04 UTC |
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| BMDB ID | BMDB0002719 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Desmosterol |
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| Description | Desmosterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, desmosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on Desmosterol. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 24-Dehydrocholesterol | ChEBI | | 3beta-Cholesta-5,24-dien-3-ol | ChEBI | | Cholesta-5,24-dien-3beta-ol | ChEBI | | 3b-Cholesta-5,24-dien-3-ol | Generator | | 3Β-cholesta-5,24-dien-3-ol | Generator | | Cholesta-5,24-dien-3b-ol | Generator | | Cholesta-5,24-dien-3β-ol | Generator | | Cholest-5,24-dien-3beta-ol | HMDB | | Cholesta-5,24-dien-3-ol | HMDB | | 24 Dehydrocholesterol | HMDB | | Demosterol | HMDB | | (3beta)-Cholesta-5,24-dien-3-ol | HMDB | | (3Β)-cholesta-5,24-dien-3-ol | HMDB | | 24,25-Dehydrocholesterol | HMDB | | Desmosterol | HMDB |
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| Chemical Formula | C27H44O |
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| Average Molecular Weight | 384.6377 |
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| Monoisotopic Molecular Weight | 384.33921603 |
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| IUPAC Name | (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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| Traditional Name | (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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| CAS Registry Number | 313-04-2 |
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| SMILES | [H][C@@]12CC[C@H]([C@H](C)CCC=C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[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/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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| InChI Key | AVSXSVCZWQODGV-DPAQBDIFSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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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 | Cholestane steroids |
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| Direct Parent | Cholesterols and derivatives |
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| Alternative Parents | |
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| Substituents | - Cholesterol-skeleton
- Cholesterol
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
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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 | 121.5 °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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| Spectra |
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| Spectra | |
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| Synthesis Reference | Kircher, Henry W.; Rosenstein, Fumiko U. Preparation of desmosterol from (20S,22R,S)-3b-acetoxychola-5,23-dien-22-ol. Journal of Organic Chemistry (1987), 52(12), 2586-8. |
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