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Identification
YMDB IDYMDB00158
NameO-Acetyl-L-homoserine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionO-Acetyl-L-homoserine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. O-Acetyl-L-homoserine is a very strong basic compound (based on its pKa). O-Acetyl-L-homoserine exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
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Synonyms
  • O-Acetyl-L-homoserine
  • O-Acetylhomoserine
CAS number7540-67-2
WeightAverage: 161.1558
Monoisotopic: 161.068807845
InChI KeyFCXZBWSIAGGPCB-YFKPBYRVSA-N
InChIInChI=1S/C6H11NO4/c1-4(8)11-3-2-5(7)6(9)10/h5H,2-3,7H2,1H3,(H,9,10)/t5-/m0/s1
IUPAC Name(2S)-4-(acetyloxy)-2-aminobutanoic acid
Traditional IUPAC NameO-acetyl-L-homoserine
Chemical FormulaC6H11NO4
SMILESCC(=O)OCC[C@H](N)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Carboxylic acid ester
  • Amino acid
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility83.9 g/LALOGPS
logP-2.9ALOGPS
logP-3.4ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)2.02ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.62 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.06 m³·mol⁻¹ChemAxon
Polarizability15.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
Sulfur metabolismec00920 Map00920
SMPDB ReactionsNot Available
KEGG Reactions
L-Cysteine + O-Acetyl-L-homoserineAcetic acid + L-Cystathionine + hydron
Acetyl-CoA + L-HomoserineCoenzyme A + O-Acetyl-L-homoserine
Methanethiol + O-Acetyl-L-homoserineL-Methionine + Acetic acid + hydron
O-Acetyl-L-homoserine + Hydrogen sulfideL-Homocysteine + Acetic acid + hydron
Glycine + alpha-D-ribose 5-phosphate + hydron + L-Cysteine + O-Acetyl-L-homoserinePyruvic acid + Acetic acid + Carbon dioxide + gamma-Aminobutyric acid + 4-Methyl-5-(2-phosphonooxyethyl)thiazole + Ammonium + water
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
  • Cherest, H., Eichler, F., Robichon-Szulmajster, H. (1969). "Genetic and regulatory aspects of methionine biosynthesis in Saccharomyces cerevisiae." J Bacteriol 97:328-336.5764336
  • Mulet, J. M., Alemany, B., Ros, R., Calvete, J. J., Serrano, R. (2004). "Expression of a plant serine O-acetyltransferase in Saccharomyces cerevisiae confers osmotic tolerance and creates an alternative pathway for cysteine biosynthesis." Yeast 21:303-312.15042590
  • Kosuge, T., Gao, D., Hoshino, T. (2000). "Analysis of the methionine biosynthetic pathway in the extremely thermophilic eubacterium Thermus thermophilus." J Biosci Bioeng 90:271-279.16232856
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16288
HMDB IDNot Available
Pubchem Compound ID439389
Kegg IDC01077
ChemSpider ID388506
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in O-acetyltransferase activity
Specific function:
Acetyl-CoA + L-homoserine = CoA + O-acetyl-L- homoserine
Gene Name:
MET2
Uniprot ID:
P08465
Molecular weight:
53659.0
Reactions
Acetyl-CoA + L-homoserine → CoA + O-acetyl-L-homoserine.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
Not Available
Uniprot ID:
Q04533
Molecular weight:
74312.70313
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
Transforms O-acetylhomoserine into homocysteine and O- acetylserine into cysteine
Gene Name:
MET17
Uniprot ID:
P06106
Molecular weight:
48671.39844
Reactions
O-acetyl-L-homoserine + methanethiol → L-methionine + acetate.
O(3)-acetyl-L-serine + H(2)S → L-cysteine + acetate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
STR2
Uniprot ID:
P47164
Molecular weight:
72349.89844
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.