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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:11:46 UTC
Update Date2022-03-07 03:17:53 UTC
HMDB IDHMDB0062381
Secondary Accession Numbers
  • HMDB62381
Metabolite Identification
Common Name4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol
Description4,4-dimethyl-8,14-cholestadien-3beta-ol, also known as 4,4-dcdo or T-MAS, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4,4-dimethyl-8,14-cholestadien-3beta-ol is considered to be a sterol lipid molecule. 4,4-dimethyl-8,14-cholestadien-3beta-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866304
Synonyms
ValueSource
(3beta,5alpha)-4,4-Dimethylcholesta-8,14-dien-3-olChEBI
4,4-Dimethyl-5alpha-cholesta-8,14-diene-3beta-olChEBI
4,4-Dimethylcholesta-8,14-dien-3-olChEBI
(3b,5a)-4,4-Dimethylcholesta-8,14-dien-3-olGenerator
(3Β,5α)-4,4-dimethylcholesta-8,14-dien-3-olGenerator
4,4-Dimethyl-5a-cholesta-8,14-diene-3b-olGenerator
4,4-Dimethyl-5α-cholesta-8,14-diene-3β-olGenerator
4,4-Dimethyl-8,14-cholestadien-3b-olGenerator
4,4-Dimethyl-8,14-cholestadien-3β-olGenerator
4,4-DCDOMeSH
4,4-Dimethyl-5 alpha-cholesta-8,14-diene-3 beta-olMeSH
4,4-Dimethylcholesta-8,14-dien-3-ol, (3beta)-isomerMeSH
T-MASMeSH
4,4-Dimethyl-5a-cholesta-8,14-dien-3b-olGenerator
4,4-Dimethyl-5α-cholesta-8,14-dien-3β-olGenerator
Chemical FormulaC29H48O
Average Molecular Weight412.702
Monoisotopic Molecular Weight412.370516166
IUPAC Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Traditional Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
CAS Registry Number19456-83-8
SMILES
[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)C(C)(C)[C@]1([H])CC3
InChI Identifier
InChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h13,19-20,22,25-26,30H,8-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1
InChI KeyOGQJUYXFIOFTMA-PBJLWWPKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00056 g/lALOGPS
LogP7.60ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP7.6ALOGPS
logP7.41ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.07 m³·mol⁻¹ChemAxon
Polarizability53.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.31931661259
DarkChem[M-H]-200.57831661259
DeepCCS[M-2H]-238.80730932474
DeepCCS[M+Na]+213.13530932474
AllCCS[M+H]+209.732859911
AllCCS[M+H-H2O]+207.732859911
AllCCS[M+NH4]+211.432859911
AllCCS[M+Na]+211.932859911
AllCCS[M-H]-208.232859911
AllCCS[M+Na-2H]-210.332859911
AllCCS[M+HCOO]-212.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)C(C)(C)[C@]1([H])CC33358.5Standard polar33892256
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)C(C)(C)[C@]1([H])CC33282.1Standard non polar33892256
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)C(C)(C)[C@]1([H])CC33324.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]1CC33185.2Semi standard non polar33892256
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]1CC33425.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pk-1009000000-92b588074f7734ee2ec62017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol GC-MS (1 TMS) - 70eV, Positivesplash10-06di-3103900000-01bc2923151262e134cf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 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 - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 10V, Positive-QTOFsplash10-01ot-0009500000-297ecf8f722d38ae479c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 20V, Positive-QTOFsplash10-06ya-3129100000-1decf3f66aa401d3199f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 40V, Positive-QTOFsplash10-0a4r-4339000000-908522121c236b714d572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 10V, Negative-QTOFsplash10-03di-0001900000-322cae85ce921a9ef9e22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 20V, Negative-QTOFsplash10-03di-0004900000-7e18591fb6a8fe32b4e52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 40V, Negative-QTOFsplash10-002b-1009000000-79dbea737a07aa6d7e542017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 10V, Positive-QTOFsplash10-03di-0003900000-fa5c6b41d22aa9fde4d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 20V, Positive-QTOFsplash10-03di-4532900000-a2e690ddc5b99952a3a02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 40V, Positive-QTOFsplash10-05mp-9453000000-21b23d053cc9b39975732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 20V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol 40V, Negative-QTOFsplash10-08fr-0015900000-4d68385974eaa70a3f8f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-8609
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound167817
PDB IDNot Available
ChEBI ID78904
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. Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
  6. O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  8. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..