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zymosterol intermediate 2 (YMDB00608)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 + NADP → zymosterol intermediate 2 + Carbon dioxide + NADPH
zymosterol intermediate 2 + NADPH + hydron → zymosterol + NADP
KEGG Reactions
NADP + zymosterol intermediate 1c ↔ zymosterol intermediate 2 + Carbon dioxide + NADPH + hydron
zymosterol intermediate 2 + NADPH + hydron → NADP + zymosterol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-ad25e0dccfe72be6cb9eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l6r-6498000000-5090eda806a93a3004e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7941000000-4022ce530acf9ad2ea96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-334e990fc728bf944c79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-6abcbf0582c0df66e719JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0009000000-75a25b37df692b4de81cJSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. 3-keto-steroid reductase
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.
Protein Details
2. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating
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.