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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:55:50 UTC
Update Date2022-03-07 02:56:13 UTC
HMDB IDHMDB0039463
Secondary Accession Numbers
  • HMDB39463
Metabolite Identification
Common Name(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol
Descriptionalpha-Tocopherol acetate, also known as a-tocopherol acetic acid or D-vitamin e acetate, belongs to the class of organic compounds known as vitamin e compounds. These are a group of fat-soluble compounds containing or derived either from a tocopherol or a tocotrienol skeleton. alpha-Tocopherol acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863380
Synonyms
ValueSource
a-Tocopherol acetateGenerator
a-Tocopherol acetic acidGenerator
alpha-Tocopherol acetic acidGenerator
Α-tocopherol acetateGenerator
Α-tocopherol acetic acidGenerator
(+)-alpha -Tocopherol acetateHMDB
(+)-alpha -Tocopheryl acetateHMDB
(+)-alpha-Tocopherol acetateHMDB
(+)-alpha-Tocopheryl acetateHMDB
(+-)-alpha-Tocopherol acetateHMDB
(2R,4'r,8'r)-alpha-Tocopherol acetateHMDB
(2R,4'r,8'r)-alpha-Tocopheryl acetateHMDB
(R,R,R)-alpha-Tocopheryl acetateHMDB
AlfacolHMDB
all-rac-alpha-Tocopheryl acetateHMDB
alpha -Tocopherol acetateHMDB
alpha -Tocopheryl acetateHMDB
alpha-Tocopherol acetate, all racHMDB
alpha-Tocopheryl acetateHMDB
Combinal eHMDB
ContopheronHMDB
Copherol 1250HMDB
Covitol 1100HMDB
Covitol 1360HMDB
D,L-alpha-Tocopheryl acetateHMDB
D-alpha -Tocopherol acetateHMDB
D-alpha -Tocopheryl acetateHMDB
D-alpha-Tocopherol acetateHMDB
D-alpha-Tocopheryl acetateHMDB
D-Vitamin e acetateHMDB
DL-alpha Tocopheryl acetateHMDB
DL-alpha-Tocopherol acetateHMDB
DL-alpha-Tocopheryl acetateHMDB
e-FerolHMDB
e-ToplexHMDB
e-VicotratHMDB
EcofrolHMDB
ECONHMDB
endo e DompeHMDB
Ephynal acetateHMDB
Epsilan-mHMDB
ErevitHMDB
FertilvitHMDB
GevexHMDB
JuvelaHMDB
O-Acetyl-alpha-tocopherolHMDB
Rovimix e 50SdHMDB
SpondyvitHMDB
Syntopherol acetateHMDB
TocopherexHMDB
Tocopherol acetateHMDB
Tocopherol acetate (JP15)HMDB
Tocopheryl acetateHMDB
TocophrinHMDB
TofaxinHMDB
Tokoferol acetateHMDB
VectanHMDB
Vitamin e acetateHMDB
Vitamin e acetate DL-formHMDB
Vitamin e acetate, ((2R*(4R*,8R*))-(+-))-isomerHMDB
Vitamin e acetate, (2R-(2R*(4R*,8R*)))-isomerHMDB
Vitamin ealpha acetateHMDB
D alpha Tocopheryl acetateMeSH
alpha Tocopherol acetateMeSH
alpha-Tocopheryl calcium succinateMeSH
alpha Tocopheryl calcium succinateMeSH
D alpha TocopherolMeSH
Tocopherol, D-alphaMeSH
D-alpha TocopherolMeSH
alpha-TocopherolMeSH
alpha Tocopherol hemisuccinateMeSH
Acetate, tocopherolMeSH
alpha TocopherolMeSH
alpha-Tocopherol succinateMeSH
Vitamin e succinateMeSH
R,R,R-alpha-TocopherolMeSH
alpha-Tocopherol hemisuccinateMeSH
3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-olMeSH
Tocopherol succinateMeSH
alpha Tocopherol succinateMeSH
6-deoxo-28-NortyphasterolHMDB
(3a,5a,22R,23R)-Cholestane-3,22,23-triolGenerator
(3Α,5α,22R,23R)-cholestane-3,22,23-triolGenerator
Chemical FormulaC27H48O3
Average Molecular Weight420.6682
Monoisotopic Molecular Weight420.360345402
IUPAC Name2-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-6-methylheptane-3,4-diol
Traditional Name2-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-6-methylheptane-3,4-diol
CAS Registry Number378795-16-5
SMILES
CC(C)CC(O)C(O)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C
InChI Identifier
InChI=1S/C27H48O3/c1-16(2)14-24(29)25(30)17(3)21-8-9-22-20-7-6-18-15-19(28)10-12-26(18,4)23(20)11-13-27(21,22)5/h16-25,28-30H,6-15H2,1-5H3
InChI KeyFHSVMYDBGPVTTJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vitamin e compounds. These are a group of fat-soluble compounds containing or derived either from a tocopherol or a tocotrienol skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentVitamin E compounds
Alternative Parents
Substituents
  • Diterpenoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • Benzenoid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point213 - 214 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP4.79ALOGPS
logP5.13ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.76ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.72 m³·mol⁻¹ChemAxon
Polarizability52.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.25131661259
DarkChem[M-H]-191.6631661259
DeepCCS[M-2H]-244.49730932474
DeepCCS[M+Na]+219.84930932474
AllCCS[M+H]+209.832859911
AllCCS[M+H-H2O]+207.832859911
AllCCS[M+NH4]+211.532859911
AllCCS[M+Na]+212.032859911
AllCCS[M-H]-204.632859911
AllCCS[M+Na-2H]-206.832859911
AllCCS[M+HCOO]-209.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triolCC(C)CC(O)C(O)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C2634.3Standard polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triolCC(C)CC(O)C(O)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C2556.3Standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triolCC(C)CC(O)C(O)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3501.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,1TMS,isomer #1CC(C)CC(O[Si](C)(C)C)C(O)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3541.3Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,1TMS,isomer #2CC(C)CC(O)C(O[Si](C)(C)C)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3518.9Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,1TMS,isomer #3CC(C)CC(O)C(O)C(C)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3554.5Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,2TMS,isomer #1CC(C)CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3512.3Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,2TMS,isomer #2CC(C)CC(O[Si](C)(C)C)C(O)C(C)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3520.7Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,2TMS,isomer #3CC(C)CC(O)C(O[Si](C)(C)C)C(C)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3499.8Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,3TMS,isomer #1CC(C)CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3439.9Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,1TBDMS,isomer #1CC(C)CC(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3754.7Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,1TBDMS,isomer #2CC(C)CC(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3745.8Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,1TBDMS,isomer #3CC(C)CC(O)C(O)C(C)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3761.9Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,2TBDMS,isomer #1CC(C)CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3980.0Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,2TBDMS,isomer #2CC(C)CC(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3956.3Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,2TBDMS,isomer #3CC(C)CC(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3936.0Semi standard non polar33892256
(3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol,3TBDMS,isomer #1CC(C)CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C4104.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfu-3019400000-3d0504e10e19753e85a52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol GC-MS (3 TMS) - 70eV, Positivesplash10-00di-2111139000-f2822bc609aa762d5a882017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 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 - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 10V, Positive-QTOFsplash10-0uki-1014900000-294ff7110522cce5609a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 20V, Positive-QTOFsplash10-0a4r-7039200000-b919696c8b60db57fed32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 40V, Positive-QTOFsplash10-0ap0-9045000000-c5df6d12f2189b0999232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 10V, Negative-QTOFsplash10-014i-0001900000-1fc796e215673e80827e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 20V, Negative-QTOFsplash10-0ldi-8229700000-77765b10f91c51d86eb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 40V, Negative-QTOFsplash10-0zgi-7019000000-3a0a3ce72982e30408f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 10V, Negative-QTOFsplash10-014i-0000900000-efcea423c2f681f5b2d92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 20V, Negative-QTOFsplash10-0gb9-2015900000-0a17d7a7bbbfa985c9912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 40V, Negative-QTOFsplash10-0gb9-4019400000-0fc9f9e7373cbefba0952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 10V, Positive-QTOFsplash10-00di-1045900000-9eab5667c1239f8ed7e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 20V, Positive-QTOFsplash10-0pvi-8396200000-5596d64d98220bbc12622021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3alpha,5alpha,22R,23R)-Cholestane-3,22,23-triol 40V, Positive-QTOFsplash10-0k95-5910000000-fece3f1b9d91d71852312021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB012538
KNApSAcK IDNot Available
Chemspider ID2033
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2117
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.