Showing metabocard for 1,25-Dihydroxyvitamin D3-26,23-lactone (BMDB0000969)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:18 UTC
Update Date2020-04-22 15:06:10 UTC
BMDB IDBMDB0000969
Secondary Accession Numbers
  • BMDB00969
Metabolite Identification
Common Name1,25-Dihydroxyvitamin D3-26,23-lactone
Description1,25-Dihydroxyvitamin D3-26,23-lactone, also known as 1,25-dihydroxycholecalciferol-26-23-lactone or 1,25-lactone, 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. Thus, 1,25-dihydroxyvitamin D3-26,23-lactone is considered to be a secosteroid. Based on a literature review a small amount of articles have been published on 1,25-Dihydroxyvitamin D3-26,23-lactone.
Structure
Thumb
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0019700000-9c2172548b380d6ca91bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-2100339000-93c90be155ad49453695View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0006900000-d3d166deef0933737d1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0628900000-cbd4e6e8feb6169622edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bti-0119000000-9899d22fda1efc4d97c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0001900000-96cd3075ec26335927e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-0002900000-127a4e586ef2392f5f68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1009000000-672ca7ea50dcc3be37c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0002900000-7a06f6703a3a6864820dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-7307900000-81146dd68ea008130635View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2603900000-3a75708441b966325516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0352900000-cf21aba2c7b98f507e68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0192200000-1be4400d7526fef77dfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0952000000-208186dd5e2d9a9323bfView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000969
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
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 ReferencesNot Available