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Identification
YMDB IDYMDB00548
Namezymosterol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionZymosterol intermediate 2, also known as zymostrol or 5a-cholesta-8,24-dien-3b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Zymosterol intermediate 2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • 5-alpha-cholesta-8,24-dien-3-beta-ol
  • 5alpha-Cholesta-8,24-dien-3beta-ol
  • delta8,24-Cholestadien-3beta-ol
  • Zymostrol
  • 5a-Cholesta-8,24-dien-3b-ol
  • 5Α-cholesta-8,24-dien-3β-ol
  • delta8,24-Cholestadien-3b-ol
  • Δ8,24-cholestadien-3β-ol
  • Zymosterol intermediic acid 2
  • Δ8,24-cholestadien-3b-ol
  • (3b,5a)- Cholesta-8,24-dien-3-ol
  • Cholest-8,24-dien-3b-ol
  • Cholesta-8,24-dien-3-ol
  • Zymosterol
CAS number7488-99-5
WeightAverage: 384.6377
Monoisotopic: 384.33921603
InChI KeyCGSJXLIKVBJVRY-XTGBIJOFSA-N
InChIInChI=1S/C27H44O/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/h7,19-21,23-24,28H,6,8-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1
IUPAC Name(2S,5S,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-ol
Traditional IUPAC Namezymosterol
Chemical FormulaC27H44O
SMILES[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](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-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point187.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
logP6.51ALOGPS
logP6.66ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity121.2 m³·mol⁻¹ChemAxon
Polarizability49.86 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
zymosterol + NADPH → 5a-Cholest-8-en-3b-ol + NADP
zymosterol → 5a-Cholesta-7,24-dien-3b-ol
zymosterol intermediate 2 + NADPH + hydronzymosterol + NADP
zymosterol + S-Adenosyl-L-methionine24-methylidene-5alpha-cholest-8-en-3beta-ol + S-Adenosylhomocysteine + hydron
zymosterol ↔ 5a-cholesta-7,24-dien-3B-ol
KEGG Reactions
zymosterol + oleoyl-CoAzymosteryl oleate + Coenzyme A
zymosterolzymosteryl palmitoleate + Coenzyme A
zymosterol intermediate 2 + NADPH + hydronNADP + zymosterol
zymosterol + oxygen + S-Adenosylmethioninewater + S-Adenosylhomocysteine + hydron + ergosta-5,7,22,24(28)-tetraen-3beta-ol
zymosterol + S-Adenosylmethionine24-methylidene-5alpha-cholest-8-en-3beta-ol + S-Adenosylhomocysteine + 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
  • 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
  • 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
  • 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:Not Available
External Links:
ResourceLink
CHEBI ID18252
HMDB IDHMDB03993
Pubchem Compound ID4369188
Kegg IDC05437
ChemSpider ID22889577
FOODB IDFDB023869
WikipediaZymosterol
BioCyc IDCPD1F-118

Enzymes

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.
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 methyltransferase activity
Specific function:
Catalyzes the methyl transfer from S-adenosyl-methionine to the C-24 of zymosterol to form fecosterol
Gene Name:
ERG6
Uniprot ID:
P25087
Molecular weight:
43430.5
Reactions
S-adenosyl-L-methionine + 5-alpha-cholesta-8,24-dien-3-beta-ol → S-adenosyl-L-homocysteine + 24-methylene-5-alpha-cholest-8-en-3-beta-ol.
General function:
Involved in C-8 sterol isomerase activity
Specific function:
Catalyzes the reaction which results in unsaturation at C-7 in the B ring of sterols
Gene Name:
ERG2
Uniprot ID:
P32352
Molecular weight:
24895.40039
Reactions
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