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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-07-11 15:07:49 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006719
Secondary Accession Numbers
  • HMDB06719
Metabolite Identification
Common Name5,6-trans-Vitamin D3
Description5,6-trans-vitamin D3 is the result of photodegradation of vitamin D3, and once formed in the skin, exposure to sunlight results in its rapid photodegradation to a variety of photoproducts. During chronic exposure to sunlight vitamin D3 in the skin can be photoisomerized to a variety of photoproducts, including 5,6-trans-vitamin D3. Because 5,6-Trans-vitamin D3 is a photoproduct of vitamin D3 and have a pseudo-1-alpha-hydroxyl structure due to the 180-degree rotation of the 3-hydroxyl group during isomerization. 5,6-trans-vitamin D3 can mimic the intestinal calcium transport activity of 1alpha,25(OH)2D (the active form of vitamine D). (PMID: 10876100 , 2541158 ).
Structure
Data?1582752401
Synonyms
ValueSource
3-[(2E)-2-[(1R,3AS,7ar)-1-[(1R)-1,5-dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanolHMDB
5,6-trans-CholecalciferolHMDB
trans-Vitamin D3HMDB
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(1S,3E)-3-{2-[(1R,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Nametrans-vitamin D3
CAS Registry Number22350-41-0
SMILES
CC(C)CCC[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1/C[C@@H](O)CCC1=C
InChI Identifier
InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13+/t21-,24+,25-,26?,27-/m1/s1
InChI KeyQYSXJUFSXHHAJI-YYJGPZIQSA-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
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP7.98ALOGPS
logP7.13ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.22 m³·mol⁻¹ChemAxon
Polarizability49.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+196.23631661259
DarkChem[M-H]-198.22831661259
DeepCCS[M-2H]-229.91330932474
DeepCCS[M+Na]+205.33830932474
AllCCS[M+H]+203.732859911
AllCCS[M+H-H2O]+201.432859911
AllCCS[M+NH4]+205.832859911
AllCCS[M+Na]+206.432859911
AllCCS[M-H]-203.432859911
AllCCS[M+Na-2H]-205.232859911
AllCCS[M+HCOO]-207.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,6-trans-Vitamin D3CC(C)CCC[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1/C[C@@H](O)CCC1=C3411.8Standard polar33892256
5,6-trans-Vitamin D3CC(C)CCC[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1/C[C@@H](O)CCC1=C3126.7Standard non polar33892256
5,6-trans-Vitamin D3CC(C)CCC[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1/C[C@@H](O)CCC1=C3256.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,6-trans-Vitamin D3,1TMS,isomer #1C=C1CC[C@H](O[Si](C)(C)C)C/C1=C\C=C1/CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CCCC(C)C3118.0Semi standard non polar33892256
5,6-trans-Vitamin D3,1TBDMS,isomer #1C=C1CC[C@H](O[Si](C)(C)C(C)(C)C)C/C1=C\C=C1/CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CCCC(C)C3340.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-trans-Vitamin D3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-3029000000-1950c74de34369a704002017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-trans-Vitamin D3 GC-MS (1 TMS) - 70eV, Positivesplash10-002f-9207800000-c6f808a014153de38d582017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-trans-Vitamin D3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 10V, Positive-QTOFsplash10-014r-0129000000-442693b5a55274aeb0b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 20V, Positive-QTOFsplash10-0c09-3496000000-bf01a7ddf350733d39f22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 40V, Positive-QTOFsplash10-0a4i-8298000000-b9136b2dd6e2c22c11232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 10V, Negative-QTOFsplash10-001i-0009000000-70ba08bf3cd328c6087e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 20V, Negative-QTOFsplash10-001i-0009000000-c16445787a057993951a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 40V, Negative-QTOFsplash10-066r-1239000000-328f37347d493ff8f54a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 10V, Negative-QTOFsplash10-001i-0009000000-603399a81fb181c574d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 20V, Negative-QTOFsplash10-001i-0109000000-b58c77cde27f58c4b0652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 40V, Negative-QTOFsplash10-00lr-1439000000-c1e928e2afe7d9751a2e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 10V, Positive-QTOFsplash10-000i-0359000000-640bd7a637465076fc862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 20V, Positive-QTOFsplash10-0kn9-6595000000-5904d0483de4db1a9d202021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 40V, Positive-QTOFsplash10-0a4i-4920000000-62ad2227e2005042715a2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024037
KNApSAcK IDNot Available
Chemspider ID35016020
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12303099
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Webb AR, DeCosta BR, Holick MF: Sunlight regulates the cutaneous production of vitamin D3 by causing its photodegradation. J Clin Endocrinol Metab. 1989 May;68(5):882-7. [PubMed:2541158 ]