Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 01:38:14 UTC |
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Update date | 2015-07-21 06:59:23 UTC |
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Primary ID | FDB028339 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (24R)-Cholest-5-ene-3-beta,24-diol |
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Description | (24R)-Cholest-5-ene-3-beta,24-diol or 24(R)-Hydroxycholesterol is a hydroxysterol. It is a substrate for Cytochrome P450 39A1 (EC 1.14.13.99), which is primarily a liver-specific enzyme. It is involved in the following reaction: (24R)-cholest-5-ene-3-beta,24-diol + NADPH + O(2) = (24R)-cholest-5-ene-3-beta,7-alpha,24-triol + NADP(+) + H(2)O. 24(R)-Hydroxycholesterol is an intermediate in bile acid metabolism. The majority of circulating 24-hydroxycholesterol in humans is made in the brain and is increased in serum of Alzheimer patients. 24(S)-Hydroxycholesterol is generally more abundant in human tissues than 24(R)-Hydroxycholesterol. It has also been shown that 24(R) and 24(S)-Hydroxycholesterols are substrates for hepatic cholesterol 7-a hydroxylase (CYP7A), leading to the production of 7-alpha hydroxylated bile acids. [HMDB] |
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CAS Number | Not Available |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C27H46O2 |
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IUPAC name | (1S,2R,5S,10S,11S,15R)-14-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol |
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InChI Identifier | InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22?,23+,24+,25-,26+,27-/m1/s1 |
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InChI Key | IOWMKBFJCNLRTC-BPWUYGJYSA-N |
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Isomeric SMILES | [H][C@@]12CCC([C@H](C)CC[C@@H](O)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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Average Molecular Weight | 402.6529 |
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Monoisotopic Molecular Weight | 402.349780716 |
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Classification |
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Description | Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. |
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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 | Bile acids, alcohols and derivatives |
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Direct Parent | Dihydroxy bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - 24-hydroxysteroid
- Dihydroxy bile acid, alcohol, or derivatives
- 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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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | (24R)-Cholest-5-ene-3-beta,24-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0076-1009000000-918c634f2e40ac4fb8c3 | Spectrum | Predicted GC-MS | (24R)-Cholest-5-ene-3-beta,24-diol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-2111290000-94668570804377216a37 | Spectrum | Predicted GC-MS | (24R)-Cholest-5-ene-3-beta,24-diol, 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, Negative | splash10-0udi-0003900000-db2e1b276e6052150b6f | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ue9-0009700000-55fe1a48489ad8aa8bb6 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ri-7009000000-7a2a5d9fa1c30ba0c55b | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0000900000-079f76b4d985e4b92c9d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-2002900000-8f2c13356a2deb497dc5 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fr2-3019200000-8713943f0050708c3c27 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f79-0009200000-0f92e092c978feb7ef4a | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-4119100000-6a8569b9873ebded521a | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0c01-5049000000-3466fdb5c0a23399bea3 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-0209100000-bfa601e19f304e87cbf0 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-07vu-4559000000-a66619fe39b0d508ca4c | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-5962000000-9419106f12041db2bda5 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 26626774 |
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ChEMBL ID | CHEMBL1867391 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 53481009 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB11643 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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