Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-21 06:12:09 UTC |
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Update Date | 2022-03-07 03:17:53 UTC |
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HMDB ID | HMDB0062385 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4α-carboxy-5α-cholesta-8,24-dien-3β-ol |
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Description | 4alpha-carboxy-zymosterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4alpha-carboxy-zymosterol is considered to be a sterol lipid molecule. 4alpha-carboxy-zymosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CCC2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)[C@@]([H])(C(O)=O)[C@]1([H])CC3 InChI=1S/C28H44O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h7,18,20-21,23-25,29H,6,8-16H2,1-5H3,(H,30,31)/t18-,20-,21?,23+,24+,25+,27-,28-/m1/s1 |
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Synonyms | Value | Source |
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4a-Carboxy-zymosterol | Generator | 4Α-carboxy-zymosterol | Generator |
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Chemical Formula | C28H44O3 |
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Average Molecular Weight | 428.657 |
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Monoisotopic Molecular Weight | 428.329045277 |
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IUPAC Name | (2S,5S,6S,7S,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid |
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Traditional Name | (2S,5S,6S,7S,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CCC2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)[C@@]([H])(C(O)=O)[C@]1([H])CC3 |
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InChI Identifier | InChI=1S/C28H44O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h7,18,20-21,23-25,29H,6,8-16H2,1-5H3,(H,30,31)/t18-,20-,21?,23+,24+,25+,27-,28-/m1/s1 |
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InChI Key | JHIWIFRQJXLNEU-CEDIQTLQSA-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-skeleton
- Steroid acid
- 4-carboxy steroid
- 3-hydroxysteroid
- 15-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxysteroid
- Beta-hydroxy acid
- Hydroxy acid
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- 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 | |
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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 | 0.0035 g/l | ALOGPS | LogP | 5.79 | 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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4??-carboxy-5??-cholesta-8,24-dien-3??-ol,1TMS,isomer #1 | CC(C)=CCC[C@@H](C)[C@H]1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C(=O)O)[C@@H]1CC3 | 3495.9 | Semi standard non polar | 33892256 | 4??-carboxy-5??-cholesta-8,24-dien-3??-ol,1TMS,isomer #2 | CC(C)=CCC[C@@H](C)[C@H]1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@H](C(=O)O[Si](C)(C)C)[C@@H]1CC3 | 3455.1 | Semi standard non polar | 33892256 | 4??-carboxy-5??-cholesta-8,24-dien-3??-ol,2TMS,isomer #1 | CC(C)=CCC[C@@H](C)[C@H]1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)[C@@H]1CC3 | 3431.9 | Semi standard non polar | 33892256 | 4??-carboxy-5??-cholesta-8,24-dien-3??-ol,1TBDMS,isomer #1 | CC(C)=CCC[C@@H](C)[C@H]1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O)[C@@H]1CC3 | 3717.0 | Semi standard non polar | 33892256 | 4??-carboxy-5??-cholesta-8,24-dien-3??-ol,1TBDMS,isomer #2 | CC(C)=CCC[C@@H](C)[C@H]1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1CC3 | 3703.2 | Semi standard non polar | 33892256 | 4??-carboxy-5??-cholesta-8,24-dien-3??-ol,2TBDMS,isomer #1 | CC(C)=CCC[C@@H](C)[C@H]1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1CC3 | 3894.4 | Semi standard non 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 - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-1009300000-c5885e8a226e6092a559 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol GC-MS (2 TMS) - 70eV, Positive | splash10-0a4i-3101390000-ea34ceaa24d2eb12b402 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-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 - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 10V, Positive-QTOF | splash10-03fr-0005900000-acffd3c76a14adc4ad09 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 20V, Positive-QTOF | splash10-03yl-2009300000-796407ee4e0f4f93946e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 40V, Positive-QTOF | splash10-07vr-3129100000-32abb57970066c9d0b4b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 10V, Negative-QTOF | splash10-004i-0004900000-1d72e4e7e1356bdce6b8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 20V, Negative-QTOF | splash10-00o0-0009500000-af0fc475137fa1d376d5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 40V, Negative-QTOF | splash10-014i-1009100000-c2073aafb657e835672f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 10V, Positive-QTOF | splash10-004i-0008900000-59e017ef5d0efe845c9b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 20V, Positive-QTOF | splash10-00or-5079700000-8d076eeca61d09f42d00 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 40V, Positive-QTOF | splash10-066v-9335000000-ac0cae94f5efedcd7972 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 10V, Negative-QTOF | splash10-0059-0008900000-70e88ae7a1e4b1b7d22b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 20V, Negative-QTOF | splash10-001i-0009000000-2a8f2107720056ebbd7c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 40V, Negative-QTOF | splash10-0159-0019000000-03f42bacbb92dc194b69 | 2021-09-22 | Wishart Lab | View Spectrum |
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