Tachysterol 3 (CHEM036143)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:15:59 UTC
Update Date2016-11-09 01:21:26 UTC
Accession NumberCHEM036143
Identification
Common NameTachysterol 3
ClassSmall Molecule
DescriptionA hydroxy seco-steroid that results from the photoisomerization of previtamin D3.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,6E)-9,10-Secocholesta-5(10),6,8-trien-3-olChEBI
(6E)-(3S)-9,10-Seco-5(10),6,8-cholestatrien-3-olChEBI
(6E)-9,10-Secocholesta-5(10),6,8-trien-3beta-olChEBI
(6E)-TacalciolChEBI
TacalciolChEBI
Tachysterol3ChEBI
(3b,6E)-9,10-Secocholesta-5(10),6,8-trien-3-olGenerator
(3Β,6E)-9,10-secocholesta-5(10),6,8-trien-3-olGenerator
(6E)-9,10-Secocholesta-5(10),6,8-trien-3b-olGenerator
(6E)-9,10-Secocholesta-5(10),6,8-trien-3β-olGenerator
Tachysterol_3HMDB
1,25-Dihydroxy-3-epi-19-nor-previtamin D3MeSH, HMDB
14-Epi-19-nortachysterolMeSH, HMDB
Previtamin D(3)MeSH, HMDB
Previtamin D(3), (3alpha,6Z)-isomerMeSH, HMDB
Tachysterol(3)MeSH, HMDB
Previtamin D(3), (3beta,6E)-isomerMeSH, HMDB
Previtamin D3MeSH, HMDB
PrecholecalciferolMeSH, HMDB
PrecalciferolMeSH, HMDB
Tachysterol 3MeSH
Chemical FormulaC27H44O
Average Molecular Mass384.638 g/mol
Monoisotopic Mass384.339 g/mol
CAS Registry Number17592-07-3
IUPAC Name(1S)-3-[(E)-2-[(1R,3aR,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 Nametachysterol3
SMILESCC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CC[C@H](O)C1
InChI IdentifierInChI=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-FMCTZRJNSA-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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Polarizability50.23 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-3029000000-a763d8761e43e391b03aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-8207900000-5e6f5c8698fcd5e9bbd8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0129000000-015a6d1d725487e37f53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-4796000000-6e3f939ebe58c4a08defSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9268000000-37051f03d804993ffff4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-8ff4cced50a3c638abbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-6c4d19908d24b76afd02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-1139000000-5cbc7e24c55d3a387d1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-f6aaa09c488a652fefd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1249000000-73f138164424c30c61f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ap0-0269000000-5f5e9ae9309d1b41b38dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac9-9788000000-f8ee07f6c9798b518324Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07m4-7940000000-ee1e441ab9c77e93bb16Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006560
FooDB IDFDB023972
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2288996
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446802
ChEBI ID166835
PubChem Compound ID5283713
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10876100
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1332420
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19028513
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=6256855
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6265564
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6275887
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=6281884
8. van de Vliervoet, J. L. J.; Westerhof, P.; Keverling Buisman, J. A.; Havinga, E. Vitamin D and related compounds. VI. The synthesis and properties of dihydrotachysterol3. Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1956), 75 1179-86.
9. 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.
10. 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.