You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00543
Nameergosterol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionErgosterol is the biological precursor to vitamin D2. Ergosterol is a component of yeast and fungal cell membranes and does not occur in plant or animal cells.
Structure
Thumb
Synonyms
  • (22E)-Ergosta-5,7,22-trien-3-ol
  • (24R)-Ergosta-5,7,22-trien-3b-ol
  • (3beta,22E)-Ergosta-5,7,22-trien-3-ol
  • (3beta,2E)-Ergosta-5,7,22-trien-3-ol
  • (3beta)-Ergosta-5,7,22-trien-3-ol
  • 24-Methylcholesta-5,7,22-trien-3b-ol
  • 24-Methylcholesta-5,7,22-trien-3beta-ol
  • 24a-Methyl-22E-dehydrocholesterol
  • 24alpha-Methyl-22E-dehydrocholestero
  • 24R-Methylcholesta-5,7,22E-trien-3b-ol
  • 24R-Methylcholesta-5,7,22E-trien-3beta-ol
  • ergosta-5,7,22-trien-3-ol
  • Ergosterin
  • Ergosterol
  • Provitamine D2
  • (22E,24S)-24-Methylcholesta-5,7,22-trien-3beta-ol
  • Provitamin D2
  • (22E,24S)-24-Methylcholesta-5,7,22-trien-3b-ol
  • (22E,24S)-24-Methylcholesta-5,7,22-trien-3β-ol
CAS number57-87-4
WeightAverage: 396.6484
Monoisotopic: 396.33921603
InChI KeyDNVPQKQSNYMLRS-APGDWVJJSA-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/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
IUPAC Name(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional IUPAC Nameergosterol
Chemical FormulaC28H44O
SMILESCC(C)[C@@H](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
DescriptionThis compound 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-beta-hydroxy-delta-7-steroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxy-delta-5-steroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point170 °C
Experimental Properties
PropertyValueReference
Water Solubility16 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
logP7.39ALOGPS
logP6.63ChemAxon
logS-6.4ALOGPS
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
Refractivity127.13 m³·mol⁻¹ChemAxon
Polarizability50.29 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cell envelope
  • lipid particle
  • 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
ergosta-5,7,22,24(28)-tetraen-3beta-ol + hydron + NADPHergosterol + NADP
KEGG Reactions
ergosterol + oleoyl-CoAergosteryl oleate + Coenzyme A
ergosterolergosteryl palmitoleate + Coenzyme A
NADPH + hydron + ergosta-5,7,22,24(28)-tetraen-3beta-olNADP + ergosterol
ergosterol + fatty acid ↔ ergosterol ester + water
Uridine diphosphate glucose + ergosterolUridine 5'-diphosphate + ergosteryl 3-beta-D-glucoside + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • 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
  • Wilcox, L. J., Balderes, D. A., Wharton, B., Tinkelenberg, A. H., Rao, G., Sturley, S. L. (2002). "Transcriptional profiling identifies two members of the ATP-binding cassette transporter superfamily required for sterol uptake in yeast." J Biol Chem 277:32466-32472.12077145
  • Schulz, T. A., Prinz, W. A. (2007). "Sterol transport in yeast and the oxysterol binding protein homologue (OSH) family." Biochim Biophys Acta 1771:769-780.17434796
  • Warnecke, D., Erdmann, R., Fahl, A., Hube, B., Muller, F., Zank, T., Zahringer, U., Heinz, E. (1999). "Cloning and functional expression of UGT genes encoding sterol glucosyltransferases from Saccharomyces cerevisiae, Candida albicans, Pichia pastoris, and Dictyostelium discoideum." J Biol Chem 274:13048-13059.10224056
  • Koffel, R., Tiwari, R., Falquet, L., Schneiter, R. (2005). "The Saccharomyces cerevisiae YLL012/YEH1, YLR020/YEH2, and TGL1 genes encode a novel family of membrane-anchored lipases that are required for steryl ester hydrolysis." Mol Cell Biol 25:1655-1668.15713625
  • Zweytick, D., Leitner, E., Kohlwein, S. D., Yu, C., Rothblatt, J., Daum, G. (2000). "Contribution of Are1p and Are2p to steryl ester synthesis in the yeast Saccharomyces cerevisiae." Eur J Biochem 267:1075-1082.10672016
Synthesis Reference:He, Xiuping; Zhang, Borun; Tan, Huarong. Overexpression of a sterol C-24(28) reductase increases ergosterol production in Saccharomyces cerevisiae. Biotechnology Letters (2003), 25(10), 773-778.
External Links:
ResourceLink
CHEBI ID16933
HMDB IDHMDB00878
Pubchem Compound ID444679
Kegg IDC01694
ChemSpider ID22889659
FOODB IDNot Available
WikipediaErgosterol
BioCyc IDERGOSTEROL

Enzymes

General function:
Involved in O-acyltransferase activity
Specific function:
Ensures probably most of the acyltransferase activity. Suppression of ARE2 reduces sterol ester levels to 25% of the normal value
Gene Name:
ARE2
Uniprot ID:
P53629
Molecular weight:
74022.20313
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
General function:
Involved in O-acyltransferase activity
Specific function:
Acyl-CoA + cholesterol = CoA + cholesterol ester
Gene Name:
ARE1
Uniprot ID:
P25628
Molecular weight:
71612.5
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
May be involved in decane metabolism and autophagy. Involved in the biosynthesis of sterol glucoside
Gene Name:
ATG26
Uniprot ID:
Q06321
Molecular weight:
136053.0
Reactions
UDP-glucose + a sterol → UDP + a sterol 3-beta-D-glucoside.
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 lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo
Gene Name:
TGL1
Uniprot ID:
P34163
Molecular weight:
62978.39844
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters, thereby playing a central role in lipid metabolism. Under heme-deficient conditions, it constitutes the major steryl ester hydrolase, suggesting that it plays a central role in mobilization of steryl esters under anaerobic conditions
Gene Name:
YEH1
Uniprot ID:
Q07804
Molecular weight:
66507.39844
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism
Gene Name:
YEH2
Uniprot ID:
Q07950
Molecular weight:
62446.0
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.

Transporters

General function:
Involved in ATP binding
Specific function:
Transporter involved in the uptake of sterol
Gene Name:
AUS1
Uniprot ID:
Q08409
Molecular weight:
157750.0
General function:
Involved in ATP binding
Specific function:
Transporter involved in the uptake of sterol
Gene Name:
PDR11
Uniprot ID:
P40550
Molecular weight:
160536.0