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 21:09:08 UTC |
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Update Date | 2020-02-26 21:26:19 UTC |
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HMDB ID | HMDB0006280 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7-a,25-Dihydroxycholesterol |
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Description | 7 alpha-hydroxylation is not directly involved, positively or negatively, in the action of 25- or 27-hydroxycholesterol as suppressors of HMG-CoA reductase activity. Human diploid fibroblasts (HDF) and the human melanoma cell line SK-MEL-2 converted 25-hydroxycholesterol into 7 alpha,25-dihydroxycholesterol and 7 alpha,25-dihydroxy-4-cholesten-3-one while the virus-transformed fibroblast line 90VA-VI, the colon carcinoma cell line WiDr and the breast cancer cell line MDA-231 did not express 7 alpha-hydroxylase activity. The 7 alpha-hydroxylation of 25-hydroxycholesterol in HDF could be stimulated by dexamethasone and cortisol and inhibited by metyrapone. An unidentified, possibly 4-hydroxylated, metabolite was formed by 90VA-VI cells and a polar, probably conjugated, metabolite was formed by WiDr cells. The 7 alpha-hydroxylated metabolites of 25-hydroxycholesterol suppressed the activity of HMG-CoA reductase to a similar extent as 25-hydroxycholesterol in HDF but not in 90VA-VI cells, while the 7 alpha-hydroxylated metabolites of 27-hydroxycholesterol suppressed the activity of HMG-CoA reductase also in 90VA-VI cells. (PMID: 9059514 ). |
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Structure | |
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Synonyms | Value | Source |
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4-oxo-all-trans-Retinoic acid | ChEBI | 4-oxo-AtRA | ChEBI | 4-oxo-all-trans-Retinoate | Generator | 4-oxo-Retinoate | Generator | 4-Keto-retinoate | HMDB | 4-Keto-retinoic acid | HMDB | 4-Ketoretinoate | HMDB | 4-Ketoretinoic acid | HMDB | 4-Oxoretinoate | HMDB | 4-Oxoretinoic acid | HMDB | 4-Oxotretinoin | HMDB | all-trans-4-Oxoretinoate | HMDB | all-trans-4-Oxoretinoic acid | HMDB | Ro 11-4824 | HMDB | Ro 12-4824 | HMDB | 4-oxo-13-cis-Retinoic acid | HMDB | 4-oxo-Isotretinoin | HMDB | 4-oxo-trans-Retinoic acid | HMDB | 4-Oxoretinoic acid, (13-cis)-isomer | HMDB | 3beta,7alpha,25-Trihydroxycholest-5-ene | ChEBI | 5-Cholesten-3beta,7alpha,25-triol | ChEBI | Cholest-5-ene-3beta,7alpha,25-triol | ChEBI | 3b,7a,25-Trihydroxycholest-5-ene | Generator | 3β,7α,25-trihydroxycholest-5-ene | Generator | 5-Cholesten-3b,7a,25-triol | Generator | 5-Cholesten-3β,7α,25-triol | Generator | Cholest-5-ene-3b,7a,25-triol | Generator | Cholest-5-ene-3β,7α,25-triol | Generator | 7-alpha,25-Dihydroxycholesterol | HMDB | 7alpha,25-Dihydroxycholesterol | HMDB, KEGG | Cholest-5-ene-3-b,7-a,25-triol | HMDB | Cholest-5-ene-3-beta,7-alpha,25-triol | HMDB | 7a,25-Dihydroxycholesterol | Generator | 7Α,25-dihydroxycholesterol | Generator |
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Chemical Formula | C27H46O3 |
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Average Molecular Weight | 418.6523 |
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Monoisotopic Molecular Weight | 418.344695338 |
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IUPAC Name | (1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol |
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Traditional Name | 7α,25-dihydroxycholesterol |
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CAS Registry Number | 64907-22-8 |
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SMILES | [H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1 |
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InChI Key | BQMSKLCEWBSPPY-IKVTXIKFSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. |
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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 | Retinoids |
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Direct Parent | Retinoids |
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Alternative Parents | |
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Substituents | - Retinoic acid
- Diterpenoid
- Retinoid skeleton
- Medium-chain fatty acid
- Cyclohexenone
- Methyl-branched fatty acid
- Branched fatty acid
- Fatty acyl
- Fatty acid
- Unsaturated fatty acid
- Ketone
- Cyclic ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Carbonyl group
- Hydrocarbon derivative
- Organic oxygen compound
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic 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 | splash10-0zfr-2149500000-545454a3fcc04ae6b581 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-00xr-2210139000-efdeb2df00f6b19d4654 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f89-0009800000-7c696ae7b6e4c320a799 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f89-1009300000-73e3b4d1757a0cdd50d4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00wc-1129000000-4f248849b872f93ee029 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0005900000-232dc04b65e6de06ebab | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00kb-0009500000-11fef3b164b139cb37b1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ul9-1009200000-b7f1840b17522a9af97e | Spectrum |
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