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Identification
YMDB IDYMDB00180
NameObtusifoliol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionObtusifoliol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Obtusifoliol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 4,4-Dimethyl-14a-hydroxymethyl-5a-cholesta-8,24-dien-3b-ol
  • 4,4-dimethyl-14alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol
CAS number16910-32-0
WeightAverage: 442.7168
Monoisotopic: 442.381080844
InChI KeyDWVYYKFZEDMMPU-UHFFFAOYSA-N
InChIInChI=1S/C30H50O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,21-22,25-26,31-32H,8,10-19H2,1-7H3
IUPAC Name11-(hydroxymethyl)-2,6,6,15-tetramethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional IUPAC Nameobtusifoliol
Chemical FormulaC30H50O2
SMILES[H]OC([H])([H])C12C3=C(C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])(C([H])([H])C2([H])[H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])C1([H])C([H])([H])C3([H])[H]
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
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.0018 g/LALOGPS
logP6.54ALOGPS
logP6.43ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)19.43ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity136.32 m³·mol⁻¹ChemAxon
Polarizability55.92 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Plasma Membrane
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
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 ID17791
HMDB IDHMDB01242
Pubchem Compound ID656449
Kegg IDC01943
ChemSpider ID570838
FOODB IDFDB004683
Wikipedia IDNot Available
BioCyc IDCPD-4568

Enzymes

General function:
Involved in iron ion binding
Specific function:
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
Gene Name:
ERG11
Uniprot ID:
P10614
Molecular weight:
60719.80078
Reactions
Obtusifoliol + 3 O(2) + 3 NADPH → 4-alpha-methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol + formate + 3 NADP(+) + 4 H(2)O.