Record Information
Version2.0
Creation Date2012-05-31 13:57:31 -0600
Update Date2015-06-03 15:54:19 -0600
Secondary Accession Numbers
  • ECMDB03011
Identification
Name:O-Acetylserine
Description:O-Acetylserine is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. O-Acetylserine is biosynthesized by acetylation of the serine by the enzyme serine transacetylase. The enzyme O-acetylserine (thiol)-lyase, using sulfide sources, converts this ester into cysteine, releaseing acetate.
Structure
Thumb
Synonyms:
  • O-acetylserine
  • Acetylserine
  • AcSer
  • O(3)-acetyl-L-serine
  • O-Acetyl-L-serine
  • O-Acetyl-Serine
  • O3-Acetyl-L-serine
  • O3-acetyl-L-serine
Chemical Formula:C5H9NO4
Weight:Average: 147.1293
Monoisotopic: 147.053157781
InChI Key:VZXPDPZARILFQX-BYPYZUCNSA-N
InChI:InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
CAS number:5147-00-2
IUPAC Name:(2S)-3-(acetyloxy)-2-aminopropanoic acid
Traditional IUPAC Name:O-acetyl-L-serine
SMILES:CC(=O)OC[C@H](N)C(O)=O
Chemical Taxonomy
DescriptionThis compound 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
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility174.0 mg/mLALOGPS
logP-2.9ALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.19 m3·mol-1ChemAxon
Polarizability13.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Secondary Metabolites: cysteine biosynthesis from serinePW000977 Pw000977Pw000977 greyscalePw000977 simple
Sulfur metabolismPW000922 Pw000922Pw000922 greyscalePw000922 simple
cysteine biosynthesisPW000800 Pw000800Pw000800 greyscalePw000800 simple
sulfur metabolism (butanesulfonate)PW000923 Pw000923Pw000923 greyscalePw000923 simple
sulfur metabolism (ethanesulfonate)PW000925 Pw000925Pw000925 greyscalePw000925 simple
sulfur metabolism (isethionate)PW000926 Pw000926Pw000926 greyscalePw000926 simple
sulfur metabolism (methanesulfonate)PW000927 Pw000927Pw000927 greyscalePw000927 simple
sulfur metabolism (propanesulfonate)PW000924 Pw000924Pw000924 greyscalePw000924 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01c0-0900000000-cbac2ae436dcca0d0251View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01c0-0900000000-7c5ef6cc55e1a01984afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-6900000000-f2863fb0291664c5ca21View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00yi-0910000000-4eb5131c64279fbabbfbView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0006-9000000000-1a24fb3faa274e72fcc5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-01c0-0900000000-cbac2ae436dcca0d0251View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-01c0-0900000000-7c5ef6cc55e1a01984afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-6900000000-f2863fb0291664c5ca21View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00yi-0910000000-4eb5131c64279fbabbfbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-006x-9300000000-048d27b5feab5a974f8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-052r-9700000000-798191f65808f670b0b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052r-9700000000-798191f65808f670b0b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uea-3900000000-ef46289d46aa69d40d48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9700000000-221b830dc83fdf079527View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-52a79cff992a3a467f06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-6900000000-4e0de865dfcc2446fe14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-5a3f4b66b56fbaca505cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-123b2507eee8f6a9f064View in MoNA
1D NMR1H NMR SpectrumNot Available
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. Pubmed: 7952062
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17981
HMDB IDHMDB03011
Pubchem Compound ID189
Kegg IDC00979
ChemSpider ID89874
WikipediaO-Acetylserine
BioCyc IDACETYLSERINE
EcoCyc IDACETYLSERINE
Ligand ExpoOAS

Enzymes

General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
metB
Uniprot ID:
P00935
Molecular weight:
41550
Reactions
O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate.
General function:
Involved in transferase activity
Specific function:
Acetyl-CoA + L-serine = CoA + O-acetyl-L- serine
Gene Name:
cysE
Uniprot ID:
P0A9D4
Molecular weight:
29316
Reactions
Acetyl-CoA + L-serine = CoA + O-acetyl-L-serine.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:
cysK
Uniprot ID:
P0ABK5
Molecular weight:
34489
Reactions
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
3-chloro-L-alanine + thioglycolate = S-carboxymethyl-L-cysteine + chloride.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
Two cysteine synthase enzymes are found. Both catalyze the same reaction. Cysteine synthase B can also use thiosulfate in place of sulfide to give cysteine thiosulfonate as a product
Gene Name:
cysM
Uniprot ID:
P16703
Molecular weight:
32664
Reactions
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Carbohydrate transport and metabolism
Specific function:
May be an export pump for cysteine and other metabolites of the cysteine pathway (such as N-acetyl-L-serine (NAS) and O- acetyl-L-serine (OAS)), and for other amino acids and their metabolites
Gene Name:
eamA
Uniprot ID:
P31125
Molecular weight:
32324
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368
General function:
Signal transduction mechanisms
Specific function:
Exporter of O-acetylserine (OAS) and cysteine
Gene Name:
eamB
Uniprot ID:
P38101
Molecular weight:
21248