14-demethyllanosterol (YMDB00604)

Identification
YMDB IDYMDB00604
Name14-demethyllanosterol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description14-demethyllanosterol, also known as 4,4-dimethylzymosterol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 14-demethyllanosterol is considered to be a sterol lipid molecule. 14-demethyllanosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (3beta,5alpha)-4,4-dimethylcholesta-8,24-dien-3-ol
  • 14-Demethyllanosterol
  • 14-desmethyllanosterol
  • 4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol
  • 4,4-Dimethyl-5alpha-cholesta-8,24-dien-3beta-ol
  • 4,4-Dimethyl-8,24-cholestadienol
  • 4,4-dimethylzymosterol
  • 4,4-Dimethylcholesta-8(9),24-dien-3beta-ol
  • (3b,5a)-4,4-Dimethylcholesta-8,24-dien-3-ol
  • (3Β,5α)-4,4-dimethylcholesta-8,24-dien-3-ol
  • 4,4-Dimethyl-5a-cholesta-8,24-dien-3b-ol
  • 4,4-Dimethyl-5α-cholesta-8,24-dien-3β-ol
  • 4,4-Dimethylcholesta-8(9),24-dien-3b-ol
  • 4,4-Dimethylcholesta-8(9),24-dien-3β-ol
CAS number59865-13-3
WeightAverage: 412.6908
Monoisotopic: 412.370516158
InChI KeyCHGIKSSZNBCNDW-QGBOJXOESA-N
InChIInChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22-,23+,25+,26+,28-,29-/m1/s1
IUPAC Name(2S,5S,7R,11R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional IUPAC Name(2S,5S,7R,11R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Chemical FormulaC29H48O
SMILES[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point148-151 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP2.92 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00054 g/LALOGPS
logP7.14ALOGPS
logP7.41ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity130.07 m³·mol⁻¹ChemAxon
Polarizability53.51 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Steroid biosynthesisPW002482 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
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, Positivesplash10-01ot-0009500000-5831f1297a9ddaefca1bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2139100000-1571d65e1b255cf2e4d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0170-3339000000-9b79492ac4a81d9025ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-e0f073ba6b1bddb613bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-276fec1a6d98e42e92a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-1009000000-9afa67f4cfe32f1b2acdJSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
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
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18364
HMDB IDNot Available
Pubchem Compound ID440559
Kegg IDC05108
ChemSpider ID25994967
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc ID44-DIMETHYL-824-CHOLESTADIENOL

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.
Protein Details
2. Delta(14)-sterol reductase
General function:
Involved in delta14-sterol reductase activity
Specific function:
Reduces the C14=C15 double bond of 4,4-dimethyl- cholesta-8,14,24-trienol to produce 4,4-dimethyl-cholesta-8,24- dienol
Gene Name:
ERG24
Uniprot ID:
P32462
Molecular weight:
50615.0
Reactions
4,4-dimethyl-5-alpha-cholesta-8,24-dien-3-beta-ol + NADP(+) → 4,4-dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol + NADPH.