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Identification
YMDB IDYMDB00605
Nameergosta-5,7,24(28)-trien-3beta-ol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Dehydroepisterol 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, 5-dehydroepisterol is considered to be a sterol lipid molecule. 5-Dehydroepisterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • Campesta-7,24(28)-dien-3beta-ol
  • Ergosta-5,7,24(28)-trien-3beta-ol
CAS numberNot Available
WeightAverage: 396.6484
Monoisotopic: 396.33921603
InChI KeyZEPNVCGPJXYABB-LOIOQLKMSA-N
InChIInChI=1S/C28H44O/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/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1
IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional IUPAC Name5-dehydroepisterol
Chemical FormulaC28H44O
SMILES[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0006 g/LALOGPS
logP7.64ALOGPS
logP6.65ChemAxon
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 Count5ChemAxon
Refractivity125.79 m³·mol⁻¹ChemAxon
Polarizability50.73 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 PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
NADH + ergosta-5,7,24(28)-trien-3beta-ol + hydron + oxygenwater + NAD + ergosta-5,7,22,24(28)-tetraen-3beta-ol
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + hydron + oxygenwater + NADP + ergosta-5,7,22,24(28)-tetraen-3beta-ol
episterol + NADPH + hydron + oxygenwater + NADP + ergosta-5,7,24(28)-trien-3beta-ol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-0019000000-ee2081ecc662ce2451e5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-2005900000-497de544ef5aa67f52beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0019000000-ec4a863acd6783c7db80JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-6159000000-2fa2d066e8ea1504f297JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-8094000000-e86c8d11fb643c8a6bd4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-03506c1fb18d95fe82baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-d3d2383799c5587a29c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2019000000-180b0828fbb1ad3d49d9JSpectraViewer
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
  • 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 ID52972
HMDB IDHMDB0006848
Pubchem Compound ID10894570
Kegg IDC15780
ChemSpider ID22889732
FOODB IDFDB024117
Wikipedia5-Dehydroepisterol
BioCyc IDNot Available

Enzymes

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.
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.
General function:
Involved in iron ion binding
Specific function:
Catalyzes the introduction of a C-5 double bond in the B ring of ergosterol. May contribute to the regulation of ergosterol biosynthesis
Gene Name:
ERG3
Uniprot ID:
P32353
Molecular weight:
42729.89844
Reactions
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.