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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 16:01:42 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006560
Secondary Accession Numbers
  • HMDB06560
Metabolite Identification
Common NameTachysterol 3
DescriptionTachysterol 3 is a normal human secosterooid metabolite from the class of vitamin D3 photoisomer derivatives. It is synthesized from 7-Dehydrocholesterol in the epidermis in response to ultraviolet irradiation. When human skin is exposed to ultraviolet radiation, epidermal 7-dehydrocholesterol is converted to previtamin D, and during prolonged exposure, the synthesis of previtamin D3 reaches a plateau at about 10 to 15 percent of the original 7-dehydrocholesterol content, and previtamin D3 is photoisomerized to two biologically inert isomers and tachysterol 3 is one of them (the other one being lumisterol 3). Therefore, tachysterol is a metabolite to chronic exposure to sunlight. Tachysterol 3, as well as other photoisomers of vitamin D3 and previtamin D3 has been demonstrated to have inhibited keratinocyte proliferation. Thus, sunlight provides vitamin D3 photoproducts that may act directly to regulate epidermal proliferation and differentiation under physiologic conditions. (PMID 6256855 , 10876100 ).
Structure
Data?1582752391
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 Weight384.6377
Monoisotopic Molecular Weight384.33921603
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
CAS Registry Number17592-07-3
SMILES
CC(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 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-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
Ontology
Not AvailableNot 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
Polarizability50.23 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]+195.87231661259
DarkChem[M-H]-195.05331661259
DeepCCS[M-2H]-237.99530932474
DeepCCS[M+Na]+212.4130932474
AllCCS[M+H]+203.932859911
AllCCS[M+H-H2O]+201.632859911
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
Tachysterol 3CC(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)C13793.5Standard polar33892256
Tachysterol 3CC(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)C13179.4Standard non polar33892256
Tachysterol 3CC(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)C13135.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tachysterol 3,1TMS,isomer #1CC1=C(/C=C/C2=CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C)CC13167.0Semi standard non polar33892256
Tachysterol 3,1TBDMS,isomer #1CC1=C(/C=C/C2=CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC13386.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tachysterol 3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-3029000000-a763d8761e43e391b03a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tachysterol 3 GC-MS (1 TMS) - 70eV, Positivesplash10-0006-8207900000-5e6f5c8698fcd5e9bbd82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tachysterol 3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tachysterol 3 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 - Tachysterol 3 10V, Positive-QTOFsplash10-014r-0129000000-015a6d1d725487e37f532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 20V, Positive-QTOFsplash10-0ab9-4796000000-6e3f939ebe58c4a08def2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 40V, Positive-QTOFsplash10-0a4i-9268000000-37051f03d804993ffff42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 10V, Negative-QTOFsplash10-001i-0009000000-8ff4cced50a3c638abba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 20V, Negative-QTOFsplash10-001i-0009000000-6c4d19908d24b76afd022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 40V, Negative-QTOFsplash10-066r-1139000000-5cbc7e24c55d3a387d1d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 10V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 20V, Negative-QTOFsplash10-001i-0009000000-f6aaa09c488a652fefd42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 40V, Negative-QTOFsplash10-001i-1249000000-73f138164424c30c61f02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 10V, Positive-QTOFsplash10-0ap0-0269000000-5f5e9ae9309d1b41b38d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 20V, Positive-QTOFsplash10-0ac9-9788000000-f8ee07f6c9798b5183242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tachysterol 3 40V, Positive-QTOFsplash10-07m4-7940000000-ee1e441ab9c77e93bb162021-09-24Wishart 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 IDFDB023972
KNApSAcK IDNot Available
Chemspider ID4446802
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2288996
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283713
PDB IDNot Available
ChEBI ID166835
Food Biomarker OntologyNot Available
VMH IDTS3
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis Referencevan 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.
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 ]