Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:48 UTC |
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HMDB ID | HMDB0000969 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 1,25-Dihydroxyvitamin D3-26,23-lactone |
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Description | 1,25-Dihydroxyvitamin D3-26,23-lactone (1,25(OH)2D3-26,23-lactone) is a vitamin D3 metabolite. The formation of 1,25(OH)2D3-26,23-lactone occurs in normocalcemic states and in situations in which 1,25(OH)2D3 has been administered. (PMID: 6324253 ). 1,25-dihydroxyvitamin D3 and (23S)-1,23,25-trihydroxyvitamin D3 are efficient precursors to 1,25(OH)2D3-26,23-lactone. 1,25(OH)2D3-26,23-lactone has an inhibitory action of bone resorption and the lactone ring plays a major part in its expression. (PMID: 6548386 , 1666030 ). |
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Structure | |
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Synonyms | Value | Source |
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1,25-Dihydroxycholecalciferol-26-23-lactone | HMDB | 1,25-Lactone | HMDB | 1alpha,25-Dihydroxyvitamin D3-26,23-lactone | HMDB | 23S,25R)-1a,25-Dihydroxyvitamin D3 26,23-lactone | HMDB | Calcitriol lactone | HMDB | Calcitriol-26,23-lactone | HMDB | 1 alpha,25-Dihydroxyvitamin D3-26,23-lactone | HMDB | 23(S),25(R)-1,25(OH)2D3-26,23-Lactone | HMDB | (23S,25R)-1a,25-Dihydroxyvitamin D3 26,23-lactone / (23S,25R)-1a,25-dihydroxycholecalciferol 26,23-lactone | HMDB | (23S,25R)-1Α,25-dihydroxyvitamin D3 26,23-lactone / (23S,25R)-1α,25-dihydroxycholecalciferol 26,23-lactone | HMDB | 1,25-Dihydroxyvitamin D3-26,23-lactone | MeSH |
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Chemical Formula | C27H40O5 |
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Average Molecular Weight | 444.6035 |
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Monoisotopic Molecular Weight | 444.28757439 |
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IUPAC Name | (3R,5S)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyloxolan-2-one |
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Traditional Name | 1,25-lactone |
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CAS Registry Number | 81203-50-1 |
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SMILES | [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)[C@H](C)C[C@H]1C[C@@](C)(O)C(=O)O1 |
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InChI Identifier | InChI=1S/C27H40O5/c1-16(12-21-15-27(4,31)25(30)32-21)22-9-10-23-18(6-5-11-26(22,23)3)7-8-19-13-20(28)14-24(29)17(19)2/h7-8,16,20-24,28-29,31H,2,5-6,9-15H2,1,3-4H3/b18-7+,19-8-/t16-,20-,21+,22-,23+,24+,26-,27-/m1/s1 |
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InChI Key | WMYIVSWWSRCZFA-RWVJFQLJSA-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 | - Triterpenoid
- Steroid lactone
- Gamma butyrolactone
- Cyclic alcohol
- Tertiary alcohol
- Tetrahydrofuran
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Carbonyl group
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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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 | splash10-004i-0019700000-9c2172548b380d6ca91b | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0002-2100339000-93c90be155ad49453695 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-056r-0006900000-d3d166deef0933737d1d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-0628900000-cbd4e6e8feb6169622ed | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0bti-0119000000-9899d22fda1efc4d97c0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0001900000-96cd3075ec26335927e7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004l-0002900000-127a4e586ef2392f5f68 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1009000000-672ca7ea50dcc3be37c4 | Spectrum |
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Synthesis Reference | Baggiolini, Enrico G.; Uskokovic, Milan R.; Wovkulich, Peter M. Process for the preparation of 1a,23,25-trihydroxycholecalciferol-26-oic acid 23,26-lactone. U.S. (1986), 10 pp. Cont.-in-part of U.S. Ser. No. 461,835, abandoned. CODEN: USXXAM US 4632784 A 19861230 CAN 107:59328 AN 1987:459328 |
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General References | - Kumar R: Metabolism of 1,25-dihydroxyvitamin D3. Physiol Rev. 1984 Apr;64(2):478-504. [PubMed:6324253 ]
- Horst RL, Wovkulich PM, Baggiolini EG, Uskokovic MR, Engstrom GW, Napoli JL: (23S)-1,23,25-Trihydroxyvitamin D3: its biologic activity and role in 1 alpha,25-dihydroxyvitamin D3 26,23-lactone biosynthesis. Biochemistry. 1984 Aug 14;23(17):3973-9. [PubMed:6548386 ]
- Kumegawa M, Ishizuka S, Sumitani K, Hiura K, Kawata T, Okawa M, Hakeda Y: Effects of 1 alpha, 25-dihydroxyvitamin D3-26,23-lactone and its intermediate metabolites on bone metabolism in vivo and in vitro. Contrib Nephrol. 1991;91:109-15. [PubMed:1666030 ]
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