Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-01-29 13:08:20 UTC
Update Date2022-03-07 02:51:12 UTC
HMDB IDHMDB0011606
Secondary Accession Numbers
  • HMDB11606
Metabolite Identification
Common Name4-alpha-Methyl-5-alpha-cholest-7-en-3-one
Description4-alpha-Methyl-5-alpha-cholest-7-en-3-one is involved in the steroid biosynthesis pathway. In this pathway, 4-alpha-methyl-5-alpha-cholest-7-en-3-one is enzymatically converted from 4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 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
(4alpha,5alpha)-4-Methylcholest-7-en-3-oneChEBI
4alpha-Methyl-5alpha-cholest-7-en-3-oneChEBI
(4a,5a)-4-Methylcholest-7-en-3-oneGenerator
(4Α,5α)-4-methylcholest-7-en-3-oneGenerator
4a-Methyl-5a-cholest-7-en-3-oneGenerator
4Α-methyl-5α-cholest-7-en-3-oneGenerator
4-a-Methyl-5-a-cholest-7-en-3-oneGenerator
4-Α-methyl-5-α-cholest-7-en-3-oneGenerator
Chemical FormulaC28H46O
Average Molecular Weight398.6642
Monoisotopic Molecular Weight398.354866094
IUPAC Name(1R,2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-one
Traditional Name(1R,2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-one
CAS Registry Number2789-43-7
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)C(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C28H46O/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/h10,18-20,22-25H,7-9,11-17H2,1-6H3/t19-,20+,22-,23+,24+,25+,27-,28+/m1/s1
InChI KeyOWKGVPXWOHLTSL-LIUJFMQASA-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-oxo-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-7-steroid
  • Delta-7-steroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility2.8e-05 g/LALOGPS
logP7.41ALOGPS
logP7.86ChemAxon
logS-7.2ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.16 m³·mol⁻¹ChemAxon
Polarizability51.34 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]+198.88431661259
DarkChem[M-H]-198.96631661259
DeepCCS[M-2H]-246.46330932474
DeepCCS[M+Na]+220.5830932474
AllCCS[M+H]+205.732859911
AllCCS[M+H-H2O]+203.632859911
AllCCS[M+NH4]+207.632859911
AllCCS[M+Na]+208.232859911
AllCCS[M-H]-206.132859911
AllCCS[M+Na-2H]-207.932859911
AllCCS[M+HCOO]-210.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-alpha-Methyl-5-alpha-cholest-7-en-3-one[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)C(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C3077.8Standard polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)C(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C3246.7Standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)C(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C3267.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@H]4[C@H](C)CCCC(C)C)C3=CC[C@@H]123297.3Semi standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@H]4[C@H](C)CCCC(C)C)C3=CC[C@@H]123192.6Standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@H]4[C@H](C)CCCC(C)C)C3=CC[C@@H]123424.0Standard polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3199.9Semi standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3123.7Standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3419.6Standard polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@H]4[C@H](C)CCCC(C)C)C3=CC[C@@H]123515.4Semi standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@H]4[C@H](C)CCCC(C)C)C3=CC[C@@H]123408.0Standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@H]4[C@H](C)CCCC(C)C)C3=CC[C@@H]123546.0Standard polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)C(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3457.7Semi standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)C(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3276.2Standard non polar33892256
4-alpha-Methyl-5-alpha-cholest-7-en-3-one,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)C(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3538.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-02nc-1029000000-187950bef8eb469baf6e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 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-one 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-alpha-Methyl-5-alpha-cholest-7-en-3-one 10V, Positive-QTOFsplash10-0002-0009000000-bb2c357db6af6080edc22016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 20V, Positive-QTOFsplash10-0537-3119000000-108e40a11672e5a5bd082016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 40V, Positive-QTOFsplash10-0api-4119000000-3ee20bc53aed6be5b57c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 10V, Negative-QTOFsplash10-0002-0009000000-28811ec09471134c13882016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 20V, Negative-QTOFsplash10-0002-0009000000-8d59ec43e25c945d61ba2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 40V, Negative-QTOFsplash10-00lr-4009000000-631cee49d3cc35670fcb2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 10V, Positive-QTOFsplash10-000t-0009000000-5d833e3bb2845348969f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 20V, Positive-QTOFsplash10-0api-6359000000-500c398bcef9a91b980b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 40V, Positive-QTOFsplash10-0a4i-9840000000-891b5c21c2070cdfce8e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 10V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 20V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-alpha-Methyl-5-alpha-cholest-7-en-3-one 40V, Negative-QTOFsplash10-0002-0009000000-30a4a83a731aa19eb43a2021-09-24Wishart 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 IDFDB028316
KNApSAcK IDNot Available
Chemspider ID389311
KEGG Compound IDC04453
BioCyc ID4-ALPHA-METHYL-5-ALPHA-CHOLEST-7-EN-3-ON
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440345
PDB IDNot Available
ChEBI ID16495
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