You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:38 UTC
HMDB IDHMDB00969
Secondary Accession NumbersNone
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
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 KeyInChIKey=WMYIVSWWSRCZFA-RWVJFQLJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing 8 isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • Steroid lactone
  • Steroid
  • Terpene lactone
  • Cyclohexanol
  • Gamma butyrolactone
  • Saccharide
  • Tertiary alcohol
  • Oxolane
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity126.15 m3·mol-1ChemAxon
Polarizability51.11 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022344
KNApSAcK IDNot Available
Chemspider ID4942850
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00969
Metagene LinkHMDB00969
METLIN IDNot Available
PubChem Compound6438368
PDB IDNot Available
ChEBI 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. [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. [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. [1666030 ]