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ergosta-5,7,22,24(28)-tetraen-3beta-ol (YMDB00606)

Identification
YMDB IDYMDB00606
Nameergosta-5,7,22,24(28)-tetraen-3beta-ol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionergosta-5,7,22,24(28)-tetraen-3-β-ol, also known as 5,7,22,24(28)-ergostatetraenol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, ergosta-5,7,22,24(28)-tetraen-3-β-ol is considered to be a sterol lipid molecule. ergosta-5,7,22,24(28)-tetraen-3-β-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (22E)-24-methylcholesta-5,7,22,24(24(1))-tetraen-3beta-ol
  • 5,7,22,24(28)-Ergostatetraenol
  • Ergosta-5,7,22,24(24(1))-tetraen-3beta-ol
  • Ergosta-5,7,22,24(241)-tetraen-3beta-ol
  • Ergosta-5,7,22,24(28)-tetraen-3beta-ol
  • (22E)-24-Methylcholesta-5,7,22,24(24(1))-tetraen-3b-ol
  • (22E)-24-Methylcholesta-5,7,22,24(24(1))-tetraen-3β-ol
  • Ergosta-5,7,22,24(24(1))-tetraen-3b-ol
  • Ergosta-5,7,22,24(24(1))-tetraen-3β-ol
  • Ergosta-5,7,22,24(241)-tetraen-3b-ol
  • Ergosta-5,7,22,24(241)-tetraen-3β-ol
  • Ergosta-5,7,22,24(28)-tetraen-3b-ol
  • Ergosta-5,7,22,24(28)-tetraen-3β-ol
CAS numberNot Available
WeightAverage: 394.6325
Monoisotopic: 394.323565966
InChI KeySQFQJKZSFOZDJY-CVGLIYDESA-N
InChIInChI=1S/C28H42O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18,20,22,24-26,29H,3,11-17H2,1-2,4-6H3/b8-7+/t20-,22+,24-,25+,26+,27+,28-/m1/s1
IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R,3E)-6-methyl-5-methylidenehept-3-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional IUPAC Name5,7,22,24(28)-ergostatetraenol
Chemical FormulaC28H42O
SMILESCC(C)C(=C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
Chemical Taxonomy
Description belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00063 g/LALOGPS
logP7.48ALOGPS
logP6.28ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity126.91 m³·mol⁻¹ChemAxon
Polarizability50.41 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
  • 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
5,7,24(28)-Ergostatrienol + hydron + NADPH + oxygen → ergosta-5,7,22,24(28)-tetraen-3beta-ol + NADP + water
ergosta-5,7,22,24(28)-tetraen-3beta-ol + hydron + NADPH → ergosterol + NADP
KEGG Reactions
NADH + ergosta-5,7,24(28)-trien-3beta-ol + hydron + oxygen → water + NAD + ergosta-5,7,22,24(28)-tetraen-3beta-ol
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + hydron + oxygen → water + NADP + ergosta-5,7,22,24(28)-tetraen-3beta-ol
NADPH + hydron + ergosta-5,7,22,24(28)-tetraen-3beta-ol → NADP + ergosterol
zymosterol + oxygen + S-Adenosylmethionine → water + S-Adenosylhomocysteine + hydron + ergosta-5,7,22,24(28)-tetraen-3beta-ol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0019000000-5dfae7f781d036269e82JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r6-3179000000-018cfcadc12d346b23e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fts-3292000000-0db2c08a85b294aa65b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7ff5ab6f1dacb99f5bd3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-4a2a9241374762d2965fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2019000000-3eac3bba4bb15c2400dfJSpectraViewer
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:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Lamb, D. C., Kelly, D. E., Manning, N. J., Kaderbhai, M. A., Kelly, S. L. (1999). "Biodiversity of the P450 catalytic cycle: yeast cytochrome b5/NADH cytochrome b5 reductase complex efficiently drives the entire sterol 14-demethylation (CYP51) reaction." FEBS Lett 462:283-288.10622712
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18249
HMDB IDNot Available
Pubchem Compound ID23724485
Kegg IDC05440
ChemSpider ID24850092
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. NADH-cytochrome b5 reductase 2
General function:
Involved in oxidoreductase activity
Specific function:
The outer membrane form may mediate the reduction of outer membrane cytochrome b5, and the soluble inter-membrane space form may transfer electrons from external NADH to cytochrome c, thereby mediating an antimycin-insensitive, energy-coupled oxidation of external NADH by yeast mitochondria. Involved in the reduction of D-erythroascorbyl free radicals
Gene Name:
MCR1
Uniprot ID:
P36060
Molecular weight:
34137.69922
Reactions
NADH + 2 ferricytochrome b5 → NAD(+) + H(+) + 2 ferrocytochrome b5.
Protein Details
2. NADPH--cytochrome P450 reductase
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5
Gene Name:
NCP1
Uniprot ID:
P16603
Molecular weight:
76771.10156
Reactions
NADPH + n oxidized hemoprotein → NADP(+) + n reduced hemoprotein.
Protein Details
3. Delta(24(24(1)))-sterol reductase
General function:
Involved in delta24(24-1) sterol reductase activity
Specific function:
Ergosterol + NADP(+) = ergosta- 5,7,22,24(24(1))-tetraen-3-beta-ol + NADPH
Gene Name:
ERG4
Uniprot ID:
P25340
Molecular weight:
56039.30078
Reactions
Ergosterol + NADP(+) → ergosta-5,7,22,24(24(1))-tetraen-3-beta-ol + NADPH.
Protein Details
4. NADH-cytochrome b5 reductase 1
General function:
Involved in oxidoreductase activity
Specific function:
Electron donor reductase for cytochrome b5. The cytochrome b5/NADH cytochrome b5 reductase electron transfer system supports the catalytic activity of several sterol biosynthetic enzymes. Plays a role in bud morphology
Gene Name:
CBR1
Uniprot ID:
P38626
Molecular weight:
31493.59961
Reactions
NADH + 2 ferricytochrome b5 → NAD(+) + H(+) + 2 ferrocytochrome b5.