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Identification
YMDB IDYMDB00652
NameO-acetyl-L-serine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionO-Acetylserine 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-Acetylserine is a very strong basic compound (based on its pKa). O-Acetylserine exists in all living species, ranging from bacteria to humans. hydrogen sulfide and O-acetylserine can be converted into L-cysteine and acetic acid; which is catalyzed by the enzymes cysteine synthase b and O-acetylserine sulfhydrylase a. In yeast, O-acetylserine is involved in the metabolic pathway called the sulfur metabolism pathway.
Structure
Thumb
Synonyms
  • L-Serine, acetate (ester)
  • O-acetyl-L-serine
  • O3-Acetyl-L-serine
  • L-Serine, acetic acid (ester)
  • O-Acetyl-serine
  • O-Acetylserine hydrobromide, (D)-isomer
  • O-Acetylserine, (L)-isomer
  • Serine acetate ester
  • O-Acetylserine
CAS number5147-00-2
WeightAverage: 147.1293
Monoisotopic: 147.053157781
InChI KeyVZXPDPZARILFQX-BYPYZUCNSA-N
InChIInChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
IUPAC Name(2S)-3-(acetyloxy)-2-aminopropanoic acid
Traditional IUPAC NameO-acetyl-L-serine
Chemical FormulaC5H9NO4
SMILESCC(=O)OC[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
  • Carboxylic acid ester
  • Amino acid
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility174 g/LALOGPS
logP-2.8ALOGPS
logP-3.4ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.19 m³·mol⁻¹ChemAxon
Polarizability13.44 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 Reactions
Hydrogen sulfide + O-acetyl-L-serineL-Cysteine + Acetic acid + hydron
KEGG Reactions
O-acetyl-L-serine + Hydrogen sulfideAcetic acid + hydron + L-Cysteine
L-Serine + Acetyl-CoACoenzyme A + O-acetyl-L-serine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01c0-0900000000-cbac2ae436dcca0d0251JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01c0-0900000000-7c5ef6cc55e1a01984afJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-6900000000-f2863fb0291664c5ca21JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00yi-0910000000-4eb5131c64279fbabbfbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01c0-0900000000-cbac2ae436dcca0d0251JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01c0-0900000000-7c5ef6cc55e1a01984afJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-6900000000-f2863fb0291664c5ca21JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00yi-0910000000-4eb5131c64279fbabbfbJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-1a24fb3faa274e72fcc5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9300000000-048d27b5feab5a974f8dJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-052r-9700000000-798191f65808f670b0b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052r-9700000000-798191f65808f670b0b8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uea-3900000000-ef46289d46aa69d40d48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9700000000-221b830dc83fdf079527JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-52a79cff992a3a467f06JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-6900000000-4e0de865dfcc2446fe14JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-5a3f4b66b56fbaca505cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-123b2507eee8f6a9f064JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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
  • Takagi, H., Yoshioka, K., Awano, N., Nakamori, S., Ono, B. (2003). "Role of Saccharomyces cerevisiae serine O-acetyltransferase in cysteine biosynthesis." FEMS Microbiol Lett 218:291-297.12586406
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17981
HMDB IDHMDB03011
Pubchem Compound ID99478
Kegg IDC00979
ChemSpider ID89874
FOODB IDFDB023094
WikipediaO-Acetylserine
BioCyc IDACETYLSERINE

Enzymes

General function:
Involved in cysteine biosynthetic process from serine
Specific function:
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:
Not Available
Uniprot ID:
P53206
Molecular weight:
42800.5
Reactions
O(3)-acetyl-L-serine + H(2)S → L-cysteine + acetate.
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.