Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-23 04:39:23 UTC |
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Update Date | 2022-03-07 03:17:57 UTC |
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HMDB ID | HMDB0062610 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (25R)-7alpha,26-dihydroxycholest-4-en-3-one |
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Description | (25R)-7alpha,26-dihydroxycholest-4-en-3-one 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 (25R)-7alpha,26-dihydroxycholest-4-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | [H][C@](C)(CO)CCC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C InChI=1S/C27H44O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h14,17-18,21-25,28,30H,5-13,15-16H2,1-4H3/t17-,18-,21-,22+,23+,24-,25+,26+,27-/m1/s1 |
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Synonyms | Value | Source |
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(7alpha,25R)-7,26-Dihydroxycholest-4-en-3-one | ChEBI | (7a,25R)-7,26-Dihydroxycholest-4-en-3-one | Generator | (7Α,25R)-7,26-dihydroxycholest-4-en-3-one | Generator | (25R)-7a,26-Dihydroxycholest-4-en-3-one | Generator | (25R)-7Α,26-dihydroxycholest-4-en-3-one | Generator | 7alpha,27-Dihydroxy-4-cholesten-3-one | MeSH | Cytosterone | MeSH |
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Chemical Formula | C27H44O3 |
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Average Molecular Weight | 416.646 |
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Monoisotopic Molecular Weight | 416.329045277 |
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IUPAC Name | (1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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Traditional Name | (1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](C)(CO)CCC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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InChI Identifier | InChI=1S/C27H44O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h14,17-18,21-25,28,30H,5-13,15-16H2,1-4H3/t17-,18-,21-,22+,23+,24-,25+,26+,27-/m1/s1 |
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InChI Key | KVJVJJWIEXCECB-OICBIKJFSA-N |
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Chemical Taxonomy |
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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 | - 26-hydroxysteroid
- Dihydroxy bile acid, alcohol, or derivatives
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 7-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Delta-4-steroid
- Fatty alcohol
- Cyclohexenone
- Fatty acyl
- Cyclic alcohol
- Secondary alcohol
- Cyclic ketone
- Ketone
- Organooxygen compound
- Primary alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Alcohol
- Organic oxide
- 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 | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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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 | 0.0029 g/l | ALOGPS | LogP | 4.60 | ALOGPS |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(25R)-7alpha,26-dihydroxycholest-4-en-3-one,1TMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O)CO[Si](C)(C)C | 3677.2 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,1TMS,isomer #2 | C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C | 3619.5 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,1TMS,isomer #3 | C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O | 3557.3 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,2TMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C | 3602.7 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,2TMS,isomer #2 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O)CO[Si](C)(C)C | 3564.3 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,2TMS,isomer #3 | C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C | 3429.1 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,3TMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C | 3442.3 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,3TMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C | 3587.8 | Standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,3TMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C | 3698.0 | Standard polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,1TBDMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O)CO[Si](C)(C)C(C)(C)C | 3916.0 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,1TBDMS,isomer #2 | C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C | 3843.8 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,1TBDMS,isomer #3 | C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O | 3781.6 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,2TBDMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C | 4063.6 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,2TBDMS,isomer #2 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O)CO[Si](C)(C)C(C)(C)C | 4022.1 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,2TBDMS,isomer #3 | C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C | 3865.6 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,3TBDMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C | 4121.6 | Semi standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,3TBDMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C | 4187.0 | Standard non polar | 33892256 | (25R)-7alpha,26-dihydroxycholest-4-en-3-one,3TBDMS,isomer #1 | C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C | 3915.2 | Standard polar | 33892256 |
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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 - (25R)-7alpha,26-dihydroxycholest-4-en-3-one GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f79-0359200000-c5e766bc8da3445acdea | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one GC-MS (2 TMS) - 70eV, Positive | splash10-0002-2422290000-28f7e14fc17b8c233d41 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 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 - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 10V, Positive-QTOF | splash10-00kb-0009200000-f13064ffc70da2c2b57d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 20V, Positive-QTOF | splash10-00l2-1009000000-f344cdc48d7b49f22d6f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 40V, Positive-QTOF | splash10-016r-3129000000-b6c48651e7e9ac09edbc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 10V, Negative-QTOF | splash10-014i-0004900000-7754503899cd9db211c4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 20V, Negative-QTOF | splash10-014j-0009600000-54c6b067e6490ab83b85 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 40V, Negative-QTOF | splash10-0674-2009000000-ceacf291ac96437f5944 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 10V, Negative-QTOF | splash10-014i-0000900000-67ea14fb7a26b9b2d929 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 20V, Negative-QTOF | splash10-014i-0004900000-8bdc86f09a28df97edf5 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 40V, Negative-QTOF | splash10-03di-0000900000-4275a326744e6035561f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 10V, Positive-QTOF | splash10-014j-0006900000-e9af662fbf3004bddaf8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 20V, Positive-QTOF | splash10-00lr-8449100000-7fca49688554cbb2acaa | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (25R)-7alpha,26-dihydroxycholest-4-en-3-one 40V, Positive-QTOF | splash10-0a4i-9740100000-166888215b2c60e56fbc | 2021-09-24 | Wishart Lab | View Spectrum |
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