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Identification
YMDB IDYMDB00606
Nameergosta-5,7,22,24(28)-tetraen-3beta-ol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionErgosta-5,7,22,24(28)-tetraen-3beta-ol is involved in steroid biosynthesis. It is converted to egosterol through the removal of a double bond on its carbon chain.
Structure
Thumb
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
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 NameNot Available
Traditional IUPAC NameNot Available
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
Physical Properties
StateNot Available
ChargeNot Available
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted PropertiesNot Available
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 + oxygenergosta-5,7,22,24(28)-tetraen-3beta-ol + NADP + water
ergosta-5,7,22,24(28)-tetraen-3beta-ol + hydron + NADPHergosterol + NADP
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
NADPH + hydron + ergosta-5,7,22,24(28)-tetraen-3beta-olNADP + ergosterol
zymosterol + oxygen + S-Adenosylmethioninewater + S-Adenosylhomocysteine + hydron + ergosta-5,7,22,24(28)-tetraen-3beta-ol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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
Pubchem Compound ID23724485
Kegg IDC05440
ChemSpider ID24850092

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 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.
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.