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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 12:26:48 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006500
Secondary Accession Numbers
  • HMDB06500
Metabolite Identification
Common NamePrevitamin D3
DescriptionPrevitamin D3, also known as tachysterol(3) or precalciferol, 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. Based on a literature review very few articles have been published on Previtamin D3.
Structure
Data?1582752387
Synonyms
ValueSource
(3beta,6Z)-9,10-Secocholesta-5(10),6,8-trien-3-olHMDB
(6Z)-(3S)-9,10-Seco-5(10),6,8-cholestatrien-3-olHMDB
Previtamin D(3)HMDB
Previtamin d_3 / precholecalciferol / (6Z)-tacalciolHMDB
Previtamin D(3), (3beta,6E)-isomerHMDB
14-Epi-19-nortachysterolHMDB
Previtamin D(3), (3alpha,6Z)-isomerHMDB
1,25-Dihydroxy-3-epi-19-nor-previtamin D3HMDB
Tachysterol(3)HMDB
PrecholecalciferolHMDB
PrecalciferolHMDB
Tachysterol 3HMDB
Previtamin D3MeSH
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(1S)-3-[(Z)-2-[(1R,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol
Traditional Name(1S)-3-[(Z)-2-[(1R,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-1,2,3,3a,6,7-hexahydroinden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol
CAS Registry Number1173-13-3
SMILES
CC(C)CCC[C@@H](C)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C/C1=C(C)CC[C@H](O)C1
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/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3/b13-12-/t21-,24+,25-,26?,27-/m1/s1
InChI KeyYUGCAAVRZWBXEQ-QEYGBBHESA-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
  • 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 Solubility0.00037 g/LALOGPS
logP7.38ALOGPS
logP7.07ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.31ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.3 m³·mol⁻¹ChemAxon
Polarizability48.05 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]+194.67331661259
DarkChem[M-H]-194.9931661259
DeepCCS[M-2H]-228.71730932474
DeepCCS[M+Na]+204.07630932474
AllCCS[M+H]+203.932859911
AllCCS[M+H-H2O]+201.532859911
AllCCS[M+NH4]+206.132859911
AllCCS[M+Na]+206.732859911
AllCCS[M-H]-204.932859911
AllCCS[M+Na-2H]-206.732859911
AllCCS[M+HCOO]-208.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Previtamin D3CC(C)CCC[C@@H](C)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C/C1=C(C)CC[C@H](O)C13793.5Standard polar33892256
Previtamin D3CC(C)CCC[C@@H](C)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C/C1=C(C)CC[C@H](O)C13179.4Standard non polar33892256
Previtamin D3CC(C)CCC[C@@H](C)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C/C1=C(C)CC[C@H](O)C13135.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Previtamin D3,1TMS,isomer #1CC1=C(/C=C\C2=CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C)CC13165.9Semi standard non polar33892256
Previtamin D3,1TBDMS,isomer #1CC1=C(/C=C\C2=CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC13387.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Previtamin D3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-3029000000-a763d8761e43e391b03a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Previtamin D3 GC-MS (1 TMS) - 70eV, Positivesplash10-0006-8207900000-5e6f5c8698fcd5e9bbd82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Previtamin 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 - Previtamin D3 10V, Positive-QTOFsplash10-014r-0129000000-015a6d1d725487e37f532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 20V, Positive-QTOFsplash10-0ab9-4796000000-6e3f939ebe58c4a08def2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 40V, Positive-QTOFsplash10-0a4i-9268000000-37051f03d804993ffff42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 10V, Negative-QTOFsplash10-001i-0009000000-8ff4cced50a3c638abba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 20V, Negative-QTOFsplash10-001i-0009000000-6c4d19908d24b76afd022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 40V, Negative-QTOFsplash10-066r-1139000000-5cbc7e24c55d3a387d1d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 10V, Positive-QTOFsplash10-0ap0-0269000000-5f5e9ae9309d1b41b38d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 20V, Positive-QTOFsplash10-0ac9-9788000000-f8ee07f6c9798b5183242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 40V, Positive-QTOFsplash10-07m4-7940000000-ee1e441ab9c77e93bb162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 10V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 20V, Negative-QTOFsplash10-001i-0009000000-f6aaa09c488a652fefd42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Previtamin D3 40V, Negative-QTOFsplash10-001i-1249000000-73f138164424c30c61f02021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB023943
KNApSAcK IDNot Available
Chemspider ID9375051
KEGG Compound IDC07711
BioCyc IDNot Available
BiGG ID2288991
Wikipedia LinkPrevitamin D3
METLIN IDNot Available
PubChem Compound11199982
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDPD3
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceVelluz, Leon; Amiard, Gaston. Precursors for vitamin D2 or calciferol and for vitamin D3. (1952), FR 999987 19520206 CAN 51:30144 AN 1957:30144
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available