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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-07-11 15:36:18 UTC
Update Date2017-12-07 01:59:34 UTC
HMDB IDHMDB0006721
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 ).
Structure
Thumb
Synonyms
ValueSource
(3b,5E,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolHMDB
(3beta,5E,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolHMDB
25-Hydroxy-5,6-trans-cholecalciferolHMDB
25-Hydroxy-5,6-trans-vitamin D3HMDB
5,6-trans-25-HydroxycholecalciferolHMDB
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
SMILES
C[C@H](CCCC(O)(C)C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C/C=C1\C[C@H](O)CCC1=C
InChI Identifier
InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11-,22-12+/t20-,23-,24-,25?,27-/m1/s1
InChI KeyJWUBBDSIWDLEOM-ZMHTYULMSA-N
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
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 Solubility0.0022 g/LALOGPS
logP6.71ALOGPS
logP5.65ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-0.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity125.06 m³·mol⁻¹ChemAxon
Polarizability50.26 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0ab9-3029000000-4c75b5cfbc422ba2a344View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-1403290000-a8eb9294a6df1ce864d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0119100000-c93e02f4cad435f61273View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aw9-1369000000-cbcc10bc94de9ec9da1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ai-5297000000-3c05eab14ebbc9c770e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-cc66843e9af0092a8e53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0009000000-3efda332aebefe04f7edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00si-1129000000-ee8ae09159fb7ba45063View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
METLIN IDNot Available
PubChem Compound53477885
PDB IDNot Available
ChEBI IDNot Available
References
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 ]