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Showing metabocard for 1,25-Dihydroxyvitamin D3-26,23-lactone (HMDB0000969)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:48 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
Data?1582752168
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.65ALOGPS
logP2.98ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.5ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity126.15 m³·mol⁻¹ChemAxon
Polarizability51.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0019700000-9c2172548b380d6ca91bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-2100339000-93c90be155ad49453695Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0006900000-d3d166deef0933737d1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0628900000-cbd4e6e8feb6169622edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bti-0119000000-9899d22fda1efc4d97c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0001900000-96cd3075ec26335927e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-0002900000-127a4e586ef2392f5f68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1009000000-672ca7ea50dcc3be37c4Spectrum
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
FoodDB 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
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 ]