4beta-(hydroxymethyl)-4alpha-methyl-5alpha-cholest-7-en-3beta-ol (YMDB00972)

Identification
YMDB IDYMDB00972
Name4beta-(hydroxymethyl)-4alpha-methyl-5alpha-cholest-7-en-3beta-ol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol, also known as 4a-methyl-4b-hydroxymethyl-5a-cholest-7-en-3b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol is considered to be a sterol. Based on a literature review very few articles have been published on 4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 4alpha-methyl-4beta-hydroxymethyl-5alpha-cholest-7-en-3beta-ol
  • 4beta-Hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol
  • 4a-Methyl-4b-hydroxymethyl-5a-cholest-7-en-3b-ol
  • 4Α-methyl-4β-hydroxymethyl-5α-cholest-7-en-3β-ol
  • 4b-Hydroxymethyl-4a-methyl-5a-cholest-7-en-3b-ol
  • 4Β-hydroxymethyl-4α-methyl-5α-cholest-7-en-3β-ol
  • 4b-(Hydroxymethyl)-4a-methyl-5a-cholest-7-en-3b-ol
  • 4Β-(hydroxymethyl)-4α-methyl-5α-cholest-7-en-3β-ol
CAS numberNot Available
WeightAverage: 430.7061
Monoisotopic: 430.381080844
InChI KeyDWEXIFLNCXYYAA-QQHSWTODSA-N
InChIInChI=1S/C29H50O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h10,19-20,22-26,30-31H,7-9,11-18H2,1-6H3/t20-,22-,23+,24+,25-,26+,27-,28-,29-/m1/s1
IUPAC Name(1R,2R,5S,6S,7R,11R,14R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional IUPAC Name(1R,2R,5S,6S,7R,11R,14R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Chemical FormulaC29H50O2
SMILES[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@@](C)(CO)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
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
  • Cholesterol-skeleton
  • Diterpenoid
  • Hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
logP6.95ALOGPS
logP6.58ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)14.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity131.26 m³·mol⁻¹ChemAxon
Polarizability55.32 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
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 (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0003900000-5251a733d657b50fbd34JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-4139600000-3ea41936e74c41e89115JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-7439100000-15d4b9cac35fedbf23beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-a7a2279b03ba73f5b3e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u1-0007900000-32e4eaa23d92762230b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1009000000-0822409434a554377d03JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0003900000-544c838c32d262777725JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ml-5519300000-22c6a491cf47078b8757JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9201000000-7af73aca9136d2958ebdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d3ddef81c134412455e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-d3ddef81c134412455e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0000900000-91c84e6010c534116b28JSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Nose, H., Miyara, T., Kushida, N., Hoshiko, S. (2002). "Isolation of temperature-sensitive Saccharomyces cerevisiae with a mutation in erg25 for C-4 sterol methyl oxidase." J Antibiot (Tokyo) 55:962-968.12546417
  • Darnet, S., Rahier, A. (2003). "Enzymological properties of sterol-C4-methyl-oxidase of yeast sterol biosynthesis." Biochim Biophys Acta 1633:106-117.12880870
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15717
HMDB IDHMDB0304207
Pubchem Compound ID5459806
Kegg IDC04814
ChemSpider ID24850085
FOODB IDFDB030549
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. C-4 methylsterol oxidase
General function:
Involved in iron ion binding
Specific function:
Catalyzes the first step in the removal of the two C-4 methyl groups of 4,4-dimethylzymosterol
Gene Name:
ERG25
Uniprot ID:
P53045
Molecular weight:
36478.89844
Reactions
4,4-dimethyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)H + O(2) → 4-beta-hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)(+) + H(2)O.
4-beta-hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)H + O(2) → 3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carbaldehyde + NAD(P)(+) + 2 H(2)O.
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carbaldehyde + NAD(P)H + O(2) → 3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD(P)(+) + H(2)O.