4-alpha-Methyl-5-alpha-cholest-7-en-3-one (YMDB00186)

Identification
YMDB IDYMDB00186
Name4-alpha-Methyl-5-alpha-cholest-7-en-3-one
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-alpha-Methyl-5-alpha-cholest-7-en-3-one, also known as (4alpha,5alpha)-4-methylcholest-7-en-3-one, 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-alpha-methyl-5-alpha-cholest-7-en-3-one is considered to be a sterol. Based on a literature review a significant number of articles have been published on 4-alpha-Methyl-5-alpha-cholest-7-en-3-one.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 4alpha-Methyl-5alpha-cholest-7-en-3-one
  • (4alpha,5alpha)-4-Methylcholest-7-en-3-one
  • (4a,5a)-4-Methylcholest-7-en-3-one
  • (4Α,5α)-4-methylcholest-7-en-3-one
  • 4a-Methyl-5a-cholest-7-en-3-one
  • 4Α-methyl-5α-cholest-7-en-3-one
  • 4-a-Methyl-5-a-cholest-7-en-3-one
  • 4-Α-methyl-5-α-cholest-7-en-3-one
CAS number2789-43-7
WeightAverage: 398.6642
Monoisotopic: 398.354866094
InChI KeyOWKGVPXWOHLTSL-LIUJFMQASA-N
InChIInChI=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
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 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
Chemical FormulaC28H46O
SMILES[H]C1=C2[C@]3([H])C([H])([H])C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])C(=O)[C@@]([H])(C([H])([H])[H])[C@]2([H])C1([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Endoplasmic Reticulum, Lipid Particle, Plasma Membrane
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02nc-1029000000-187950bef8eb469baf6eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-bb2c357db6af6080edc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0537-3119000000-108e40a11672e5a5bd08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-4119000000-3ee20bc53aed6be5b57cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-28811ec09471134c1388JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-8d59ec43e25c945d61baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-4009000000-631cee49d3cc35670fcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0009000000-5d833e3bb2845348969fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-6359000000-500c398bcef9a91b980bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9840000000-891b5c21c2070cdfce8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d939JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d939JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0009000000-30a4a83a731aa19eb43aJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16495
HMDB IDHMDB11606
Pubchem Compound ID440345
Kegg IDC04453
ChemSpider ID24850087
FOODB IDFDB028316
Wikipedia IDNot Available
BioCyc ID4-ALPHA-METHYL-5-ALPHA-CHOLEST-7-EN-3-ON

Enzymes

Protein Details
1. 3-keto-steroid reductase
General function:
Involved in binding
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols. Also facilitates the association of ERG7 with lipid particles preventing its digestion in the endoplasmic reticulum and the lipid particles
Gene Name:
ERG27
Uniprot ID:
Q12452
Molecular weight:
39724.39844
Reactions
4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NADP(+) → 4-alpha-methyl-5-alpha-cholest-7-en-3-one + NADPH.
Protein Details
2. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest- 7-ene-4-alpha-carboxylate + NAD(P)(+) = 4-alpha-methyl-5-alpha- cholest-7-en-3-one + CO(2) + NAD(P)H
Gene Name:
ERG26
Uniprot ID:
P53199
Molecular weight:
38706.10156
Reactions
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD(P)(+) → 4-alpha-methyl-5-alpha-cholest-7-en-3-one + CO(2) + NAD(P)H.