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Identification
YMDB IDYMDB00290
Name4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol, also known as 14-demethyllanosterol or 4,4-dimethyl-8,24-cholestadienol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • (3beta,5alpha)-4,4-dimethylcholesta-8,24-dien-3-ol
  • 14-demethyllanosterol
  • 4,4-dimethyl-5 alpha -cholesta-8,24-dien-3 beta -ol
  • 4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol
  • 4,4-dimethyl-5-alpha-cholesta-8,24-dien-3-beta-ol
  • 4,4-dimethyl-5a-cholesta-8,24-dien-3b-ol
  • 4,4-dimethyl-5alpha -cholesta-8,24-dien-3-beta -ol
  • 4,4-Dimethyl-5alpha-cholest-7-en-3beta-ol
  • 4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol
  • 4,4-dimethyl-8,24-cholestadienol
  • 4,4-dimethylzymosterol
  • 4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol, (3beta)-isomer
CAS number7448-02-4
WeightAverage: 412.6908
Monoisotopic: 412.370516158
InChI KeyCHGIKSSZNBCNDW-GKBRUXRCSA-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,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional IUPAC Name(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Chemical FormulaC29H48O
SMILES[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@]2(C3=C(C([H])([H])C([H])([H])[C@@]2([H])C1(C([H])([H])[H])C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])C([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@@]1(C([H])([H])[H])C([H])([H])C3([H])[H])C([H])([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
  • 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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability53.19 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
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
SMPDB Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH → 4,4-Dimethyl-5a-cholesta-8-en-3b-ol + NADP
4,4-Dimethylcholesta-8,14,24-trienol + NADPH4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + oxygen → 4a-Methylzymosterol-4-carboxylic acid + NADP + water
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + hydron + oxygen + NADPH4alpha-methylzymosterol + water + NADP
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + hydron + oxygen + NADPH4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + NADP + water
KEGG Reactions
4,4-Dimethylcholesta-8,14,24-trienol + NADPH + hydronNADP + 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol
oxygen + 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + hydron + NADPH4beta-methylzymosterol-4alpha-carboxylic acid + NADP + water
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 ID18364
HMDB IDHMDB01286
Pubchem Compound ID165609
Kegg IDC05108
ChemSpider ID25994967
FOODB IDFDB022534
Wikipedia IDNot Available
BioCyc ID44-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET

Enzymes

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.
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.
General function:
Involved in iron ion binding
Specific function:
Required for hydroxylation of C-4 in the sphingoid moiety of ceramide. Involved in the response to syringomycin
Gene Name:
SUR2
Uniprot ID:
P38992
Molecular weight:
40734.0
Reactions