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Identification
YMDB IDYMDB00608
Namezymosterol intermediate 2
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5α-cholesta-8,24-dien-3-one, also known as zymosterone, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5α-cholesta-8,24-dien-3-one is considered to be a sterol lipid molecule. 5α-cholesta-8,24-dien-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • (3b,5a)- Cholesta-8,24-dien-3-ol
  • 5-alpha-Cholesta-8,24-dien-3-beta-ol
  • 5alpha-Cholesta-8,24-dien-3beta-ol
  • Cholest-8,24-dien-3b-ol
  • Cholest-8,24-dien-3beta-ol
  • Cholesta-8,24-dien-3-ol
  • delta8,24-Cholestadien-3beta-ol
  • Zymosterol
  • Zymosterone
CAS number128-33-6
WeightAverage: 382.6218
Monoisotopic: 382.323565966
InChI KeyAUNLIRXIJAVBNM-ZSBATXSLSA-N
InChIInChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-20,23-24H,6,8-17H2,1-5H3/t19-,20+,23-,24+,26+,27-/m1/s1
IUPAC Name(2S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one
Traditional IUPAC Name5α-cholesta-8,24-dien-3-one
Chemical FormulaC27H42O
SMILES[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)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 point110 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00071 g/LALOGPS
logP6.92ALOGPS
logP6.87ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)19.96ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity120.17 m³·mol⁻¹ChemAxon
Polarizability48.85 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
4α-carboxy-5α-cholesta-8,24-dien-3β-ol + NADPzymosterol intermediate 2 + Carbon dioxide + NADPH
zymosterol intermediate 2 + NADPH + hydronzymosterol + NADP
KEGG Reactions
NADP + zymosterol intermediate 1czymosterol intermediate 2 + Carbon dioxide + NADPH + hydron
zymosterol intermediate 2 + NADPH + hydronNADP + zymosterol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-fafef18f6f1e438c21d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-017i-1129000000-2006cfbeb2221efe1222JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-4139000000-16eafffededcd9fa4600JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-06c184e2361b4ee6c5b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-8b4140bf264b853e09feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gba-3019000000-d44463d2ecf3bc057e66JSpectraViewer
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
  • Loubbardi, A., Marcireau, C., Karst, F., Guilloton, M. (1995). "Sterol uptake induced by an impairment of pyridoxal phosphate synthesis in Saccharomyces cerevisiae: cloning and sequencing of the PDX3 gene encoding pyridoxine (pyridoxamine) phosphate oxidase." J Bacteriol 177:1817-1823.7896706
Synthesis Reference:Dolle, Roland E.; Schmidt, Stanley J.; Kruse, Lawrence I. Synthesis of zymosterol: salient intermediate of fungal and mammalian sterol biosynthesis. Journal of the Chemical Society, Chemical Communications (1988), (1), 19-21.
External Links:
ResourceLink
CHEBI ID52386
HMDB IDHMDB06271
Pubchem Compound ID92746
Kegg IDC05437
ChemSpider ID24850070
FOODB IDFDB030588
WikipediaZymosterol
BioCyc IDZYMOSTEROL

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.