Showing metabocard for 24R,25-Dihydroxyvitamin D3 (BMDB0006226)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:35 UTC
Update Date2020-04-22 15:16:59 UTC
BMDB IDBMDB0006226
Secondary Accession Numbers
  • BMDB06226
Metabolite Identification
Common Name24R,25-Dihydroxyvitamin D3
Description24R,25-Dihydroxyvitamin D3, also known as 24R,25-dihydroxycholecalciferol or secalciferol, 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. 24R,25-Dihydroxyvitamin D3 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SecalciferolHMDB
(24R)-24,25-Dihydroxyvitamin D3HMDB
(24R)-HydroxycalcidiolHMDB
24(R),25-DihydroxycholecalciferolHMDB
K-DRHMDB
Osteo DHMDB
24,25 Dihydroxyvitamin D 3HMDB
24,25-Dihydroxyvitamin D 3HMDB
24R,25-DihydroxycholecalciferolHMDB
24,25-Dihydroxyvitamin D3HMDB
24,25 Dihydroxyvitamin D3HMDB
24,25-DihydroxycholecalciferolHMDB
24,25-Dihydroxyvitamin D 3, (3beta,5Z,7E,24R)-isomerHMDB
Dihydroxyvitamin D3, 24,25HMDB
24,25 DihydroxycholecalciferolHMDB
24R,25 DihydroxycholecalciferolHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(3R,6R)-6-[(1R,4E,7aR)-4-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
Traditional Name24R,25-dihydroxyvitamin D3
CAS Registry Number55721-11-4
SMILES
C[C@H](CC[C@@H](O)C(O)(C)C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
InChI Identifier
InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24?,25-,27-/m1/s1
InChI KeyFCKJYANJHNLEEP-AOWQBJNISA-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
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.47ALOGPS
logP4.58ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.42 m³·mol⁻¹ChemAxon
Polarizability50.5 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-0a4i-7029200000-c84dd427774a8bd55bf4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1312049000-f6115b14a152464f5e1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-0119200000-7bcd78fea8093a8230aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-2369100000-04f3fb5d7d655a9ce470View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-4389100000-269c6b355710e7dcd9b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0004900000-7bbe3ea5eae60b2a2059View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mk-0009300000-4137913e2e1e7271894cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-9006000000-b2d6915fde38c349870aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006226
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023846
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-709
BiGG ID2289319
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477805
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceSeki, Masao; Koizumi, Naoyuki; Morisaki, Masuo; Ikekawa, Nobuo. Synthesis of active forms of vitamin D. VI. Synthesis of (24R)- and (24S)-24,25-dihydroxyvitamin D3. Tetrahedron Letters (1975), (1), 15-18.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available