Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-22 21:16:34 UTC |
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Update Date | 2020-02-26 21:26:19 UTC |
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HMDB ID | HMDB0006283 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 20alpha-Hydroxycholesterol |
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Description | 20alpha-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 20alpha-hydroxycholesterol is considered to be a sterol lipid molecule. 20alpha-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | |
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Synonyms | Value | Source |
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20a-Hydroxycholesterol | Generator | 20Α-hydroxycholesterol | Generator | (3beta,20R)-Cholest-5-ene-3,20-diol | HMDB | 20-Hydroxycholesterol | HMDB | 20alpha-Hydroxy cholesterol | HMDB | 20-Hydroxycholesterol, (3beta,20 xi)-isomer | HMDB | 20-Hydroxycholesterol, 3H-labeled, (3beta,20 xi)-isomer | HMDB | 20R-Hydroxycholesterol | HMDB | (20S)-20-Hydroxycholesterol | HMDB | (20S)-Cholest-5-ene-3 beta,20-diol | HMDB | 20 alpha-Hydroxycholesterol | HMDB |
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Chemical Formula | C27H46O2 |
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Average Molecular Weight | 402.6529 |
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Monoisotopic Molecular Weight | 402.349780716 |
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IUPAC Name | (1S,2R,5S,10S,11S,14S,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol |
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Traditional Name | 20a-hydroxy cholesterol |
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CAS Registry Number | 516-72-3 |
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SMILES | CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
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InChI Identifier | InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1 |
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InChI Key | MCKLJFJEQRYRQT-MGNSQDQZSA-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
- 20-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- 3-beta-hydroxysteroid
- Delta-5-steroid
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen 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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-007c-1139000000-2c00b5523723b960fa5a | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-001i-3011490000-84aa9e3675270a653af2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f79-0009200000-78634a50a076fbe30975 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05tr-3039100000-08dfa0b5e30063e9930a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0avi-8189000000-c3bb06d3d099c9c4f440 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0003900000-4b881293f669607058cc | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ue9-1039800000-4c4801e96fa5d9126da5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-059i-3089000000-806365cc5d181d0d25d9 | Spectrum |
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