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
Creation Date2007-07-11 15:36:18 UTC
Update Date2017-08-16 04:45:16 UTC
Secondary Accession Numbers
  • HMDB06721
Metabolite Identification
Common Name5,6-trans-25-Hydroxyvitamin D3
Description5,6-trans-25-Hydroxyvitamin D3 is a vitamin D3 derivative, and is found in normal plasma. 5,6-trans-25-Hydroxyvitamin D3 is a 25-hydroxylated metabolite of the secosteroid that is active in inhibiting 3H-thymidine incorporation into cultured normal human keratinocytes. The evidence strongly supports the existence of a heretofore unknown metabolic route in vitamin DS metabolism, namely, the conversion of 5,6-cis compounds to 5,6-trans compounds. The mechanism of this transformation is not clear at present; it could be enzymatic or nonenzymatic. The site of formation of 5,6-trans-25-hydroxyvitamin D3 is unknown. (PMID 6256855 , 10876100 , 6270082 ).
25-Hydroxy-5,6-trans-vitamin D3HMDB
Chemical FormulaC27H44O2
Average Molecular Weight400.6371
Monoisotopic Molecular Weight400.334130652
IUPAC Name(1R,3E)-3-{2-[(1R,4Z,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Name5,6-trans-25-hydroxyvitamin D3
CAS Registry Number36149-00-5
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as vitamin d and derivatives. These 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
  • 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
StatusExpected but not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0022 mg/mLALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-0.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity125.06 m3·mol-1ChemAxon
Polarizability50.26 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 IDFDB024039
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0006721
METLIN IDNot Available
PubChem Compound53477885
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceAndrews, David R.; Barton, Derek H. R.; Hesse, Robert H.; Pechet, Maurice M. Synthesis of 25-hydroxy- and 1a,25-dihydroxy vitamin D3 from vitamin D2 (calciferol). Journal of Organic Chemistry (1986), 51(25), 4819-28.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Holick MF, MacLaughlin JA, Doppelt SH: Regulation of cutaneous previtamin D3 photosynthesis in man: skin pigment is not an essential regulator. Science. 1981 Feb 6;211(4482):590-3. [PubMed:6256855 ]
  2. Chen TC, Persons KS, Lu Z, Mathieu JS, Holick MF: An evaluation of the biologic activity and vitamin D receptor binding affinity of the photoisomers of vitamin D3 and previtamin D3. J Nutr Biochem. 2000 May;11(5):267-72. [PubMed:10876100 ]
  3. Kumar R, Nagubandi S, Jardine I, Londowski JM, Bollman S: The isolation and identification of 5,6-trans-25-hydroxyvitamin D3 from the plasma of rats dosed with vitamin D3. Evidence for a novel mechanism in the metabolism of vitamin D3. J Biol Chem. 1981 Sep 25;256(18):9389-92. [PubMed:6270082 ]