3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde (YMDB00870)

Identification
YMDB IDYMDB00870
Name3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde is considered to be a sterol lipid molecule. 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3beta-Hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde
  • 3b-Hydroxy-4b-methyl-5a-cholest-7-ene-4a-carbaldehyde
  • 3Β-hydroxy-4β-methyl-5α-cholest-7-ene-4α-carbaldehyde
CAS numberNot Available
WeightAverage: 428.6902
Monoisotopic: 428.36543078
InChI KeyHCOOTBJPHHNRCV-AQTSNUJDSA-N
InChIInChI=1S/C29H48O2/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/h10,18-20,22-26,31H,7-9,11-17H2,1-6H3/t20-,22-,23+,24+,25-,26+,27-,28-,29+/m1/s1
IUPAC Name(1R,2R,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-ene-6-carbaldehyde
Traditional IUPAC Name(1R,2R,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-ene-6-carbaldehyde
Chemical FormulaC29H48O2
SMILES[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@](C)(C=O)[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
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • 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 Solubility8.2e-05 g/LALOGPS
logP7.02ALOGPS
logP6.89ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)14.54ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity130.28 m³·mol⁻¹ChemAxon
Polarizability54.51 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_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0002900000-fc83c15baeee66dc2f33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-7249800000-54de49fee4d385a98c1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdl-8339200000-59a084a9c6f06e708070JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-e307448367f62515e7baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-10acde02b18050e0b7dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fs-4009500000-eac12f140953d6304540JSpectraViewer
References
References:
  • 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
  • Darnet, S., Rahier, A. (2003). "Enzymological properties of sterol-C4-methyl-oxidase of yeast sterol biosynthesis." Biochim Biophys Acta 1633:106-117.12880870
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16286
HMDB IDNot Available
Pubchem Compound ID25200723
Kegg IDC11509
ChemSpider ID24850083
FOODB IDNot Available
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.