Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:09 UTC |
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HMDB ID | HMDB0001286 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol |
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Description | 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol (14-demethyllanosterol) is an intermediate in sterol biosynthesis. In particular, it is an intermediate in the conversion of lanosterol to zymosterol. 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is a substrate for C-4 methyl sterol oxidase, NAD(P)-dependent steroid dehydrogenase, Cytochrome P450 51A1 and Delta(14)-sterol reductase. |
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Structure | [H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12C InChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1 |
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Synonyms | Value | Source |
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(3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol | HMDB | 14-Demethyllanosterol | HMDB | 4,4-Dimethyl-5 alpha -cholesta-8,24-dien-3 beta -ol | HMDB | 4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol | HMDB | 4,4-Dimethyl-5-alpha-cholesta-8,24-dien-3-beta-ol | HMDB | 4,4-Dimethyl-5a-cholesta-8,24-dien-3b-ol | HMDB | 4,4-Dimethyl-5alpha -cholesta-8,24-dien-3-beta -ol | HMDB | 4,4-Dimethyl-5alpha-cholest-7-en-3beta-ol | HMDB | 4,4-Dimethyl-5alpha-cholesta-8,24-dien-3beta-ol | HMDB | 4,4-Dimethyl-8,24-cholestadienol | HMDB | 4,4-Dimethylzymosterol | HMDB | 4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol, (3beta)-isomer | HMDB |
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Chemical Formula | C29H48O |
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Average Molecular Weight | 412.6908 |
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Monoisotopic Molecular Weight | 412.370516158 |
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IUPAC Name | (2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol |
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Traditional Name | (2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol |
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CAS Registry Number | 7448-02-4 |
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SMILES | [H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1 |
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InChI Key | CHGIKSSZNBCNDW-GKBRUXRCSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Triterpenoids |
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Direct Parent | Triterpenoids |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Cholesterol-skeleton
- Cholestane-skeleton
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- 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 | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol GC-MS (Non-derivatized) - 70eV, Positive | splash10-01pk-1009000000-715a7edb03ab16ddaa67 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol GC-MS (1 TMS) - 70eV, Positive | splash10-06di-3003900000-b4d1997a0f59b226076e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 10V, Positive-QTOF | splash10-01ot-0009500000-5831f1297a9ddaefca1b | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 20V, Positive-QTOF | splash10-03dj-2139100000-1571d65e1b255cf2e4d3 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 40V, Positive-QTOF | splash10-0170-3339000000-9b79492ac4a81d9025ec | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 10V, Negative-QTOF | splash10-03di-0002900000-e0f073ba6b1bddb613bc | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 20V, Negative-QTOF | splash10-03di-0005900000-276fec1a6d98e42e92a1 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 40V, Negative-QTOF | splash10-002b-1009000000-9afa67f4cfe32f1b2acd | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 10V, Negative-QTOF | splash10-03di-0000900000-363450e12a0ea926276e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 20V, Negative-QTOF | splash10-03di-0000900000-363450e12a0ea926276e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 40V, Negative-QTOF | splash10-08fs-1015900000-96469d6e79efcdc91ee9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 10V, Positive-QTOF | splash10-03di-0009700000-803cd9d3863583645c29 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 20V, Positive-QTOF | splash10-053r-9527100000-d4f09426d4583ec16d0b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 40V, Positive-QTOF | splash10-0a4u-9743000000-3166c978b6fe24ddec4b | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-17 | Wishart Lab | View Spectrum |
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