Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:18:43 UTC |
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Update Date | 2020-05-21 16:28:43 UTC |
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BMDB ID | BMDB0000032 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7-Dehydrocholesterol |
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Description | 7-Dehydrocholesterol, also known as 5,7-cholestadien-3-b-ol or provitamin D3, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrocholesterol is considered to be a sterol lipid molecule. 7-Dehydrocholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7-Dehydrocholesterol is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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(3beta)-Cholesta-5,7-dien-3-ol | ChEBI | 5,7-Cholestadien-3-beta-ol | ChEBI | 5,7-Cholestadien-3beta-ol | ChEBI | Provitamin D3 | ChEBI | Cholesta-5,7-dien-3beta-ol | Kegg | (3b)-Cholesta-5,7-dien-3-ol | Generator | (3Β)-cholesta-5,7-dien-3-ol | Generator | 5,7-Cholestadien-3-b-ol | Generator | 5,7-Cholestadien-3-β-ol | Generator | 5,7-Cholestadien-3b-ol | Generator | 5,7-Cholestadien-3β-ol | Generator | Cholesta-5,7-dien-3b-ol | Generator | Cholesta-5,7-dien-3β-ol | Generator | (-)-7-Dehydrocholesterol | HMDB | 10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol | HMDB | 17-(1,5-Dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | HMDB | 5,7-Cholestandien-3-ol | HMDB | 5,7-Cholestandien-3beta-ol | HMDB | 7,8-Dehydro-cholesterol | HMDB | 7,8-Didehydrocholesterol | HMDB | 7-Dehydro-cholesterol | HMDB | 7-Dehydrocholesterin | HMDB | 7DHC | HMDB | Cholesta-5,7-dien-3 beta -ol | HMDB | Cholesta-5,7-dien-3-beta-ol | HMDB | Cholesta-5,7-dien-3-ol | HMDB | Dehydrocholesterin | HMDB | Dehydrocholesterol | HMDB | Delta5,7-Cholestadien-3beta-ol | HMDB | Delta5,7-Cholesterol | HMDB | Delta7-Cholesterol | HMDB | Provitamin-D3 | HMDB | Provitamin D(3) | HMDB | Cholesta-5,7-dien-3 beta-ol | HMDB | 7-Dehydrocholesterol, (3beta,10alpha)-isomer | HMDB | 7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomer | HMDB | 7-DHC | HMDB | 7-Dehydrocholesterol, (3alpha)-isomer | HMDB | 7-Dehydrocholesterol, (3beta,9beta)-isomer | 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,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-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)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol |
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CAS Registry Number | 434-16-2 |
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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)CCCC(C)C |
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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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1 |
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InChI Key | UCTLRSWJYQTBFZ-DDPQNLDTSA-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
- Cholesterol-skeleton
- 3-hydroxy-delta-5-steroid
- 3-hydroxy-delta-7-steroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- Delta-7-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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 | 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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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0axr-1019000000-73894a6c7b7346b2d1b0 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-002f-3005900000-c63a75d6ed190e98a35b | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0009000000-124abe0c8995f883f002 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-05oa-4942000000-dbfe3e996983256b1e0c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-05o0-5900000000-8115f37d8da9a1d6f5d8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 26V, negative | splash10-000i-0090000000-3645f0c0605ff7c97405 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0019000000-d2b535e3c3ed257f2215 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ar9-3139000000-87132b4b12416fa4f01e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-5249000000-257a8915fd5fab2dfaaa | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-8ff4cced50a3c638abba | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0009000000-6d9a73d8f487e848e538 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ldi-1019000000-eb1f58f2c9df95716640 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0009000000-5cafb4a46516e1c4ca5a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ktr-9168000000-27f4addc4e70c9e3fc88 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9510000000-fce215a9f0a5b16bb81c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-0009000000-cf419f92ab7dfef8f2f8 | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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