| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:33:51 UTC |
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| Updated at | 2022-05-11 16:33:51 UTC |
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| NP-MRD ID | NP0086889 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Trihydroxycoprostanoic acid |
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| Description | Trihydroxycoprostanoic acid, also known as 3,7,12-trihydroxycoprostanate or 5-thca, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Trihydroxycoprostanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, trihydroxycoprostanoic acid is involved in cerebrotendinous xanthomatosis (ctx). Trihydroxycoprostanoic acid is excreted in the urine of patients with Zellweger syndrome (PMID 7347441 ), a genetic disorder. Trihydroxycoprostanoic acid was first documented in 1981 (PMID: 7347441). Trihydroxycoprostanoic acid has been found to be associated with the diseases such as d-bifunctional protein deficiency; also trihydroxycoprostanoic acid has been linked to several inborn metabolic disorders including peroxisomal biogenesis defect and adrenoleukodystrophy (PMID: 3568406). |
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| Structure | [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2(C[C@H](O)CC[C@]12C)C(O)=O InChI=1S/C28H48O5/c1-16(2)7-6-8-17(3)19-9-10-20-24-21(13-23(31)27(19,20)5)26(4)12-11-18(29)14-28(26,25(32)33)15-22(24)30/h16-24,29-31H,6-15H2,1-5H3,(H,32,33)/t17-,18-,19-,20+,21+,22-,23+,24+,26-,27-,28+/m1/s1 |
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| Synonyms | | Value | Source |
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| Trihydroxycoprostanoate | Generator | | (3a,5b,7a,12a)-3,7,12-Trihydroxy-cholestane-5-carboxylate | HMDB | | (3a,5b,7a,12a)-3,7,12-Trihydroxy-cholestane-5-carboxylic acid | HMDB | | (3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestane-5-carboxylate | HMDB | | (3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestane-5-carboxylic acid | HMDB | | 3,7,12-Trihydroxycoprostanate | HMDB | | 3,7,12-Trihydroxycoprostanic acid | HMDB | | 3alpha,7alpha,12alpha-Trihydroxycoprostanate | HMDB | | 3alpha,7alpha,12alpha-Trihydroxycoprostanic acid | HMDB | | 5-Thca | HMDB | | Tryhydroxycoprostanate | HMDB | | Tryhydroxycoprostanic acid | HMDB | | 3 alpha,7 alpha,12 alpha-Trihydroxy-5 beta-cholestanoic acid | HMDB | | 3 alpha,7 alpha,12 alpha-Trihydroxycoprostanic acid | HMDB | | (1S,2R,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-7-carboxylate | HMDB |
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| Chemical Formula | C28H48O5 |
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| Average Mass | 464.6777 Da |
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| Monoisotopic Mass | 464.35017 Da |
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| IUPAC Name | (1S,2R,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-7-carboxylic acid |
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| Traditional Name | (1S,2R,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-7-carboxylic acid |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2(C[C@H](O)CC[C@]12C)C(O)=O |
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| InChI Identifier | InChI=1S/C28H48O5/c1-16(2)7-6-8-17(3)19-9-10-20-24-21(13-23(31)27(19,20)5)26(4)12-11-18(29)14-28(26,25(32)33)15-22(24)30/h16-24,29-31H,6-15H2,1-5H3,(H,32,33)/t17-,18-,19-,20+,21+,22-,23+,24+,26-,27-,28+/m1/s1 |
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| InChI Key | JIFNDZCDNLFAKC-YAODFNMUSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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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
- Steroid acid
- 3-hydroxysteroid
- 12-hydroxysteroid
- Hydroxysteroid
- 3-alpha-hydroxysteroid
- 7-hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Polyol
- Carboxylic acid derivative
- Organooxygen compound
- Alcohol
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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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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