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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-01-29 13:04:30 UTC
Update Date2017-12-07 02:31:51 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
Thumb
Synonyms
ValueSource
4-a-Methyl-5-a-cholest-7-en-3-b-olHMDB
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
MethostenolMeSH
4-Methylcholest-7-en-3-ol, (3beta,4alpha)-isomerMeSH
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[8.7.0.0²,⁷.0¹¹,¹⁵]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[8.7.0.0²,⁷.0¹¹,¹⁵]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
DescriptionThis compound belongs to the class of chemical entities known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Multicellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physiological effect

Health effect:

  Health condition:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Polarizability51.92 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0019000000-b3855a576db40116f521View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-3003900000-c96a5b17a00bc37a8b46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0019500000-64e64b40ea3194651304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m89-3139100000-39856e46d4ab78dd6ff7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c29-6339000000-06492203c05ed6a86cddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-f6492eb67404432e3c04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-f9d70a523634f6b0b263View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-1009000000-2cda5b422edc920fed65View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012028
KNApSAcK IDC00003659
Chemspider ID25994938
KEGG Compound IDC08825
BioCyc IDCPD-5847
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound50990062
PDB IDNot Available
ChEBI ID18378
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