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Identification
YMDB IDYMDB00609
Name3-dehydro-4-methylzymosterol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-dehydro-4-methylzymosterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 3-dehydro-4-methylzymosterol is considered to be a sterol lipid molecule. 3-dehydro-4-methylzymosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • (5alpha)-4-methylcholesta-8,24-dien-3-one
  • 3-Keto-4-methylzymosterol
  • 4-Methyl-5alpha-cholesta-8(9),24-dien-3-one
  • (5a)-4-Methylcholesta-8,24-dien-3-one
  • (5Α)-4-methylcholesta-8,24-dien-3-one
  • 4-Methyl-5a-cholesta-8(9),24-dien-3-one
  • 4-Methyl-5α-cholesta-8(9),24-dien-3-one
  • 4alpha-Methyl-5alpha-cholesta-8,24-dien-3-one
  • 4a-Methyl-5a-cholesta-8,24-dien-3-one
  • 4Α-methyl-5α-cholesta-8,24-dien-3-one
CAS numberNot Available
WeightAverage: 396.6484
Monoisotopic: 396.33921603
InChI KeyDBPZYKHQDWKORQ-MWEYQPRESA-N
InChIInChI=1S/C28H44O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20?,22-,23+,24+,27-,28+/m1/s1
IUPAC Name(2S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one
Traditional IUPAC Name3-keto-4-methylzymosterol
Chemical FormulaC28H44O
SMILES[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)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 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-skeleton
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.00056 g/LALOGPS
logP7.22ALOGPS
logP7.41ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity124.75 m³·mol⁻¹ChemAxon
Polarizability50.83 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 ReactionsNot Available
KEGG Reactions
NAD + 4beta-methylzymosterol-4alpha-carboxylic acidNADH + 3-dehydro-4-methylzymosterol + Carbon dioxide + hydron
3-dehydro-4-methylzymosterol + NADPH + hydronNADP + 4alpha-methylzymosterol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-00d160bd3605d4c8b846JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00pv-1119000000-e5a9171fb6049ee63431JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015i-2119000000-6b021eb86e51393d9798JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-e91a27c7e4df70239c24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-766b7ce92b3bc6de20e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-3009000000-b4ba7e91fae9c3e7a4baJSpectraViewer
References
References:
  • 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 ID50593
HMDB IDNot Available
Pubchem Compound ID23724597
Kegg IDC15816
ChemSpider ID21865766
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD-4578

Enzymes

General function:
Involved in binding
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols. Also facilitates the association of ERG7 with lipid particles preventing its digestion in the endoplasmic reticulum and the lipid particles
Gene Name:
ERG27
Uniprot ID:
Q12452
Molecular weight:
39724.39844
Reactions
4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NADP(+) → 4-alpha-methyl-5-alpha-cholest-7-en-3-one + NADPH.
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest- 7-ene-4-alpha-carboxylate + NAD(P)(+) = 4-alpha-methyl-5-alpha- cholest-7-en-3-one + CO(2) + NAD(P)H
Gene Name:
ERG26
Uniprot ID:
P53199
Molecular weight:
38706.10156
Reactions
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD(P)(+) → 4-alpha-methyl-5-alpha-cholest-7-en-3-one + CO(2) + NAD(P)H.