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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:48 UTC
HMDB IDHMDB00532
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetylglycine
DescriptionN-Acetylglycine is used is in biological research of peptidomimetics. It is used as the blocking agent of the N-terminus to prepare unnatural and unusual amino acids and amino acid analogs as well as to modify peptides. N-Substituted glycine analogs are widely used in peptidomimetics and drug research. Excessive amounts N-acetyl amino acids including N-acetylglycine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, Nacetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine) can be detected in the urine with individuals with Acylase I defiency. This enzyme is involved in the degradation of N-acylated proteins. Individuals with this disorder will experience convulsions, hearing loss ond difficulty feeding.
Structure
Thumb
Synonyms
ValueSource
2-AcetamidoacetateChEMBL
N-AcetylglycineChEMBL
acetylamino-Acetic acidChEMBL
2-Acetamidoacetic acidGenerator
acetylamino-AcetateGenerator
15N-Acetylglycine a-radicalHMDB
Ac glyHMDB
AcetamidoacetateHMDB
Acetamidoacetic acidHMDB
AceturateHMDB
Aceturic acidHMDB
AcetylaminoacetateHMDB
Acetylaminoacetic acidHMDB
AcetylglycocollHMDB
EthanoylaminoethanoateHMDB
Ethanoylaminoethanoic acidHMDB
N-Acetyl-glycineHMDB
N-Acetylglycine sodium saltHMDB
Chemical FormulaC4H7NO3
Average Molecular Weight117.1033
Monoisotopic Molecular Weight117.042593095
IUPAC Name2-acetamidoacetic acid
Traditional Nameaceturate
CAS Registry Number543-24-8
SMILES
CC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)
InChI KeyInChIKey=OKJIRPAQVSHGFK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point207 - 209 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility26.3 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility51.3 mg/mLALOGPS
logP-0.89ALOGPS
logP-1.3ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.45 m3·mol-1ChemAxon
Polarizability10.69 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-MS (1 TMS)splash10-0ff1-0900000000-7f59efc7318abb307de5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9000000000-e0f8be2f6c11bf3ffb19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-b3dd5f7718c7ca2f137aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-7b4e818e7fb8f7ad37feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-9300000000-fa29c9711fbb33529360View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-9700000000-a6a0c2dacd758a89690eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9100000000-41073c517efcd76b3e9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-9000000000-3586ff7ce2dbe6b00d8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-9800000000-4671448e0c1ab50647adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-9300000000-0903cfde2598dd206fd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-3804a2ffeab504193078View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified69.7 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified109.44 +/- 85.64 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified56.76 +/- 35.67 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified170 +/- 18 nmol/mmol creatinineInfant (0-1 year old)MaleAminoacylase I deficiency details
Associated Disorders and Diseases
Disease References
Aminoacylase I deficiency
  1. Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2. [16274666 ]
  2. A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. [16351159 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022100
KNApSAcK IDNot Available
Chemspider ID10507
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00532
Metagene LinkHMDB00532
METLIN ID5517
PubChem Compound10972
PDB IDAAC
ChEBI ID40410
References
Synthesis ReferenceLin, Jiang Jen; Knifton, John F.; Yeakey, Ernest L. Preparation of N-acetylglycine. U.S. (1990), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055