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Record Information
Version3.6
Creation Date2006-05-22 15:12:26 UTC
Update Date2017-03-02 21:27:09 UTC
HMDB IDHMDB03011
Secondary Accession NumbersNone
Metabolite Identification
Common NameO-Acetylserine
DescriptionO-Acetylserine (OASS) is an acylated amino acid derivative. It is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. Its presence in humans arises from either microbial metabolism in the gut or through consumption of foods containing OASS.
Structure
Thumb
Synonyms
ValueSource
L-Serine, acetate (ester)ChEBI
O3-Acetyl-L-serineChEBI
L-Serine, acetic acid (ester)Generator
O-Acetyl-L-serineHMDB
O-Acetyl-serineHMDB
O-Acetylserine hydrobromide, (D)-isomerMeSH
O-Acetylserine, (L)-isomerMeSH
Serine acetate esterMeSH
Chemical FormulaC5H9NO4
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
IUPAC Name(2S)-3-(acetyloxy)-2-aminopropanoic acid
Traditional NameO-acetyl-L-serine
CAS Registry Number5147-00-2
SMILES
CC(=O)OC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
InChI KeyVZXPDPZARILFQX-BYPYZUCNSA-N
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-052r-9700000000-798191f65808f670b0b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified24.7 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023094
    KNApSAcK IDNot Available
    Chemspider ID89874
    KEGG Compound IDC00979
    BioCyc IDACETYLSERINE
    BiGG IDNot Available
    Wikipedia LinkO-Acetylserine
    NuGOwiki LinkHMDB03011
    Metagene LinkHMDB03011
    METLIN ID3270
    PubChem Compound99478
    PDB IDOAS
    ChEBI ID17981
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
    2. 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 ]