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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:07 UTC
HMDB IDHMDB0000969
Secondary Accession Numbers
  • HMDB00969
Metabolite Identification
Common Name1,25-Dihydroxyvitamin D3-26,23-lactone
Description1,25-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 ).
Structure
Thumb
Synonyms
ValueSource
1,25-Dihydroxycholecalciferol-26-23-lactoneHMDB
1,25-LactoneHMDB
1alpha,25-Dihydroxyvitamin D3-26,23-lactoneHMDB
23S,25R)-1a,25-Dihydroxyvitamin D3 26,23-lactoneHMDB
Calcitriol lactoneHMDB
Calcitriol-26,23-lactoneHMDB
1 alpha,25-Dihydroxyvitamin D3-26,23-lactoneHMDB
23(S),25(R)-1,25(OH)2D3-26,23-LactoneHMDB
(23S,25R)-1a,25-Dihydroxyvitamin D3 26,23-lactone / (23S,25R)-1a,25-dihydroxycholecalciferol 26,23-lactoneHMDB
(23S,25R)-1Α,25-dihydroxyvitamin D3 26,23-lactone / (23S,25R)-1α,25-dihydroxycholecalciferol 26,23-lactoneHMDB
1,25-Dihydroxyvitamin D3-26,23-lactoneMeSH
Chemical FormulaC27H40O5
Average Molecular Weight444.6035
Monoisotopic Molecular Weight444.28757439
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
Traditional Name1,25-lactone
CAS Registry Number81203-50-1
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
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
InChI KeyWMYIVSWWSRCZFA-RWVJFQLJSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022344
KNApSAcK IDNot Available
Chemspider ID4942850
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438368
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBaggiolini, 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
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kumar R: Metabolism of 1,25-dihydroxyvitamin D3. Physiol Rev. 1984 Apr;64(2):478-504. [PubMed:6324253 ]
  2. 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 ]
  3. 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 ]