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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-01-29 13:04:30 UTC
Update Date2022-03-07 02:51:12 UTC
HMDB IDHMDB0011605
Secondary Accession Numbers
  • HMDB11605
Metabolite Identification
Common Name4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol
Description4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol is involved in the steroid biosynthesis pathway. In this pathway, 4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol is enzymatically converted to 4-alpha-methyl-5-alpha-cholest-7-en-3-one via the enzyme 3-keto-steroid reductase (EC: 1.1.1.270) and the cofactor NADP(+). This enzyme is responsible for the reduction of the keto group on the C-3 of sterols. (Pathway Commons). Steroid biosynthesis is an anabolic metabolic pathway that produces steroids from simple precursors. This pathway is carried out in different ways in animals than in many other organisms, making the pathway a common target for antibiotics and other anti-infective drugs. In addition, steroid metabolism in humans is the target of cholesterol-lowering drugs such as statins. (Wikipedia).
Structure
Data?1582752928
Synonyms
ValueSource
4-a-Methyl-5-a-cholest-7-en-3-b-olGenerator
4-Α-methyl-5-α-cholest-7-en-3-β-olGenerator
4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-olHMDB
4-Methylcholest-7-en-3-olHMDB
4alpha-Methyl-5alpha-cholest-7-en-3beta-olHMDB
LophenolHMDB
MethostenolHMDB
4-Methylcholest-7-en-3-ol, (3beta,4alpha)-isomerHMDB
Chemical FormulaC28H48O
Average Molecular Weight400.6801
Monoisotopic Molecular Weight400.370516158
IUPAC Name(1R,2S,5S,6S,7S,11R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional Name(1R,2S,5S,6S,7S,11R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number481-25-4
SMILES
[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC[C@@]2([H])[C@H](C)[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C28H48O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h10,18-20,22-26,29H,7-9,11-17H2,1-6H3/t19-,20+,22?,23+,24+,25+,26+,27-,28+/m1/s1
InChI KeyLMYZQUNLYGJIHI-DOQVYVCQSA-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 ParentsNot Available
SubstituentsNot Available
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 Solubility3.0e-05 g/LALOGPS
logP7.34ALOGPS
logP7.48ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.09 m³·mol⁻¹ChemAxon
Polarizability51.94 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]+199.00231661259
DarkChem[M-H]-201.29731661259
DeepCCS[M-2H]-244.59930932474
DeepCCS[M+Na]+219.70530932474
AllCCS[M+H]+206.732859911
AllCCS[M+H-H2O]+204.732859911
AllCCS[M+NH4]+208.632859911
AllCCS[M+Na]+209.232859911
AllCCS[M-H]-204.232859911
AllCCS[M+Na-2H]-206.232859911
AllCCS[M+HCOO]-208.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC[C@@]2([H])[C@H](C)[C@@H](O)CC[C@]12C2726.4Standard polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC[C@@]2([H])[C@H](C)[C@@H](O)CC[C@]12C3296.0Standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC[C@@]2([H])[C@H](C)[C@@H](O)CC[C@]12C3286.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol,1TMS,isomer #1CC(C)CCC[C@@H](C)C1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3285.6Semi standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)C1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3514.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0019000000-b3855a576db40116f5212017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-3003900000-c96a5b17a00bc37a8b462017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ldm-6930100000-54c907bb02d027ff3a672018-05-25Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 10V, Positive-QTOFsplash10-0f89-0019500000-64e64b40ea31946513042016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 20V, Positive-QTOFsplash10-0m89-3139100000-39856e46d4ab78dd6ff72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 40V, Positive-QTOFsplash10-0c29-6339000000-06492203c05ed6a86cdd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 10V, Negative-QTOFsplash10-0002-0009000000-f6492eb67404432e3c042016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 20V, Negative-QTOFsplash10-0002-0009000000-f9d70a523634f6b0b2632016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 40V, Negative-QTOFsplash10-0159-1009000000-2cda5b422edc920fed652016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 10V, Negative-QTOFsplash10-0002-0009000000-e5e9af9914ac05de1a5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 20V, Negative-QTOFsplash10-0002-0009000000-e5e9af9914ac05de1a5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 40V, Negative-QTOFsplash10-0002-0009000000-a552eca38d290506e1fb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 10V, Positive-QTOFsplash10-0ue9-0009500000-6bf6b9dc9d0fac79d65c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 20V, Positive-QTOFsplash10-0pi3-9735200000-27e52b55f97f0f7b82992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol 40V, Positive-QTOFsplash10-0a4i-8961000000-2191a8194cd396a341282021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB012028
KNApSAcK IDC00003659
Chemspider ID25994938
KEGG Compound IDC08825
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound50990062
PDB IDNot Available
ChEBI ID18378
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..

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77