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Human Metabolome Database Version 3.5

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Showing metabocard for Aminomalonic acid (HMDB01147)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:33 -0600
HMDB ID HMDB01147
Secondary Accession Numbers None
Metabolite Identification
Common Name Aminomalonic acid
Description Aminomalonic acid (Ama) was first detected in alkaline hydrolysates of proteins in 1984. Ama has been isolated from proteins of Escherichia coli and human atherosclerotic plaque. The presence of Ama has important biological implications because the malonic acid moiety potentially imparts calcium binding properties to protein. Ama is not formed from any of the 20 major amino acids during the hydrolysis procedure. Furthermore, the amount of Ama found does not depend on the presence of small amounts of O2 during the hydrolysis. No artifactual formation of ama has been demonstrated and may indeed be a constituent of proteins before the hydrolysis procedure. Possible origins of Ama include errors in protein synthesis and oxidative damage to amino acid residues in proteins. (PMID: 1621954 Link_out, 6366787 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. a-Aminomalonic acid
  2. alpha-Aminomalonic acid
  3. Amino-Malonic acid
  4. Amino-Propanedioate
  5. Amino-Propanedioic acid
  6. Aminomalonate
  7. Aminomalonic acid
  8. Aminopropanedioate
  9. Aminopropanedioic acid
Chemical Formula C3H5NO4
Average Molecular Weight 119.0761
Monoisotopic Molecular Weight 119.021857653
IUPAC Name 2-aminopropanedioic acid
Traditional IUPAC Name 2-aminopropanedioic acid
CAS Registry Number 1068-84-4
SMILES NC(C(O)=O)C(O)=O
InChI Identifier InChI=1S/C3H5NO4/c4-1(2(5)6)3(7)8/h1H,4H2,(H,5,6)(H,7,8)
InChI Key JINBYESILADKFW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • amino dicarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 126 g/L ALOGPS
LogP -3.50 ALOGPS
LogP -3.4 ChemAxon
LogS 0.03 ALOGPS
pKa (strongest acidic) 0.45 ChemAxon
pKa (strongest basic) 8.5 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 100.62 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 21.98 ChemAxon
Polarizability 9.48 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022451
KNApSAcK ID Not Available
Chemspider ID 90998 Link_out
KEGG Compound ID C00872 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01147 Link_out
Metagene Link HMDB01147 Link_out
METLIN ID Not Available
PubChem Compound 100714 Link_out
PDB ID FGL Link_out
ChEBI ID 17475 Link_out
References
Synthesis Reference Matthew, Margaret; Neuberger, A. Aminomalonate. I.U.B. (Intern. Union Biochem.) Symp. Ser. (1963), Volume Date 1962, 30 243-51.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Copley SD, Frank E, Kirsch WM, Koch TH: Detection and possible origins of aminomalonic acid in protein hydrolysates. Anal Biochem. 1992 Feb 14;201(1):152-7. Pubmed: 1621954 Link_out
  2. Van Buskirk JJ, Kirsch WM, Kleyer DL, Barkley RM, Koch TH: Aminomalonic acid: identification in Escherichia coli and atherosclerotic plaque. Proc Natl Acad Sci U S A. 1984 Feb;81(3):722-5. Pubmed: 6366787 Link_out