Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-23 10:53:13 UTC |
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Update Date | 2021-09-14 15:40:07 UTC |
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HMDB ID | HMDB0006472 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Calcitroic acid |
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Description | Calcitroic acid (1 alpha-hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)) is a metabolite of 1 alpha, 25-dihydroxyvitamin D(3) (calcitriol). It is soluble in water, and is excreted in urine. This deactivation process involves a series of oxidation reactions at C24 and C23 leading to side-chain cleavage and, ultimately, formation of the calcitroic acid. This deactivation involves the loss of carbons 24, 25, 26, and 27 and the oxidation of carbon 23 to a carboxylic acid. Calcitroic acid is also a major terminal product for the deactivation of 1α,25-dihydroxyvitamin D2. Both the kidney and the intestine metabolize 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway according to the following steps: 1,25-dihydroxyvitamin D3----1,24,25-trihydroxyvitamin D3----1,25-dihydroxy-24-oxovitamin D3-----1,23,25-trihydroxy-24-oxovitamin D3 (PMID: 2719932 ). The C-24 oxidation pathway leading to the formation of calcitroic acid has been reported to be present in bone cells, but the C-23 oxidation pathway leading to the formation of 1 alpha, 25-(OH)2D3-26,23-lactone has not been described in bone cells, even though 1 alpha, 25-(OH)2D3-26,23-lactone is noted to have a significant effect on bone formation. (PMID: 7664636 ). |
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Structure | [H][C@@]12CC[C@H]([C@H](C)CC(O)=O)[C@@]1(C)CCC\C2=C/C=C1\C[C@@H](O)C[C@H](O)C1=C InChI=1S/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7+/t14-,18-,19-,20+,21+,23-/m1/s1 |
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Synonyms | Value | Source |
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Calcitroate | Generator | (3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoate | HMDB | (3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acid | HMDB | (3R)-3-[(1R,3AS,4E,7ar)-4-[(2Z)-2-[(3R,5S)-3,5-dihydroxy-2 methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoate | HMDB | (3R)-3-[(1R,3AS,4E,7ar)-4-[(2Z)-2-[(3R,5S)-3,5-dihydroxy-2 methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoic acid | HMDB | 1 alpha-Hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3) | HMDB | 1a-Hydroxycalcioate | HMDB | 1a-Hydroxycalcioic acid | HMDB | 1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-Oate | HMDB | 1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-Oic acid | HMDB | 1alpha-Hydroxy-23-carboxytetranorvitamin D | HMDB | Calcitroic acid (D3) | HMDB | 1 alpha,3 beta-Dihydroxy-24-nor-9,10- seco-5,7,10(19)-cholatrien-23-Oic acid | HMDB | 1 alpha-Hydroxy-23-carboxytetranorvitamin D | HMDB | (3R)-3-[(1R,3AS,4E,7ar)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoate | HMDB | Calcitroic acid | HMDB |
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Chemical Formula | C23H34O4 |
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Average Molecular Weight | 374.5137 |
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Monoisotopic Molecular Weight | 374.245709576 |
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IUPAC Name | (3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoic acid |
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Traditional Name | (3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]butanoic acid |
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CAS Registry Number | 71204-89-2 |
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SMILES | [H][C@@]12CC[C@H]([C@H](C)CC(O)=O)[C@@]1(C)CCC\C2=C/C=C1\C[C@@H](O)C[C@H](O)C1=C |
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InChI Identifier | InChI=1S/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7+/t14-,18-,19-,20+,21+,23-/m1/s1 |
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InChI Key | MBLYZRMZFUWLOZ-WLWRUGSRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. |
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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 | Vitamin D and derivatives |
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Direct Parent | Vitamin D and derivatives |
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Alternative Parents | |
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Substituents | - Polycyclic triterpenoid
- Triterpenoid
- Branched fatty acid
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Fatty acyl
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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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 | Solid |
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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 | Not Available | Not Available | LogP | Not Available | Not Available |
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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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Calcitroic acid,1TMS,isomer #1 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O | 3222.9 | Semi standard non polar | 33892256 | Calcitroic acid,1TMS,isomer #2 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3166.9 | Semi standard non polar | 33892256 | Calcitroic acid,1TMS,isomer #3 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3180.8 | Semi standard non polar | 33892256 | Calcitroic acid,2TMS,isomer #1 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3158.3 | Semi standard non polar | 33892256 | Calcitroic acid,2TMS,isomer #2 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3166.1 | Semi standard non polar | 33892256 | Calcitroic acid,2TMS,isomer #3 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3125.4 | Semi standard non polar | 33892256 | Calcitroic acid,3TMS,isomer #1 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3137.6 | Semi standard non polar | 33892256 | Calcitroic acid,1TBDMS,isomer #1 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O | 3469.8 | Semi standard non polar | 33892256 | Calcitroic acid,1TBDMS,isomer #2 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 3374.8 | Semi standard non polar | 33892256 | Calcitroic acid,1TBDMS,isomer #3 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3374.7 | Semi standard non polar | 33892256 | Calcitroic acid,2TBDMS,isomer #1 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 3611.7 | Semi standard non polar | 33892256 | Calcitroic acid,2TBDMS,isomer #2 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3600.3 | Semi standard non polar | 33892256 | Calcitroic acid,2TBDMS,isomer #3 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3536.7 | Semi standard non polar | 33892256 | Calcitroic acid,3TBDMS,isomer #1 | C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3764.5 | Semi standard non polar | 33892256 |
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