Aminomalonic acid (CHEM022419)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:32:09 UTC
Update Date2016-11-09 01:17:30 UTC
Accession NumberCHEM022419
Identification
Common NameAminomalonic acid
ClassSmall Molecule
DescriptionAn amino dicarboxylic acid that is malonic acid in which one of the methylene hydrogens has been replaced by an amino group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Aminomalonic acidChEBI
AminomalonateChEBI
2-AminomalonateGenerator
a-Aminomalonic acidHMDB
alpha-Aminomalonic acidHMDB
amino-Malonic acidHMDB
amino-PropanedioateHMDB
amino-Propanedioic acidHMDB
AminopropanedioateHMDB
Aminopropanedioic acidHMDB
Chemical FormulaC3H5NO4
Average Molecular Mass119.076 g/mol
Monoisotopic Mass119.022 g/mol
CAS Registry Number1068-84-4
IUPAC Name2-aminopropanedioic acid
Traditional Nameaminomalonic acid
SMILESNC(C(O)=O)C(O)=O
InChI IdentifierInChI=1S/C3H5NO4/c4-1(2(5)6)3(7)8/h1H,4H2,(H,5,6)(H,7,8)
InChI KeyJINBYESILADKFW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Amino acid
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility126 g/LALOGPS
logP-3.5ALOGPS
logP-3.4ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)0.45ChemAxon
pKa (Strongest Basic)8.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.98 m³·mol⁻¹ChemAxon
Polarizability9.48 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-2910000000-56ddccdbe51afd85dd6cSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2910000000-56ddccdbe51afd85dd6cSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0012-1920000000-706a1afd4a87657ef924Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-9200000000-a92a1873b06d13a3cb1bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-7910000000-820eb39fc624884c77c9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05i0-9000000000-6da4c50b66acac061cd8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-081c80e5b8aaa8f7ba34Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00fr-9000000000-4dbbb4215703aa499e1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-8900000000-ce915814c1e82c9da3e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-c4dc8ccb28224391491fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-dda49c2194c794dfeebbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-b31a9403ea30555205e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-5900000000-8f53ff3974857296fab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-179c8f28fed467f08059Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9200000000-2cbb45bb0d131a8a5a4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-6bf2575f705bcef140f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-1f92eb692a3016f51886Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-2c6e9d09fa238ac1618cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9400000000-ce7be9ee668d87a767bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9000000000-a28af5b62f46a4285ac2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02289
HMDB IDHMDB0001147
FooDB IDFDB022451
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDAMINOMALONATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID90998
ChEBI ID17475
PubChem Compound ID100714
Kegg Compound IDC00872
YMDB IDNot Available
ECMDB IDECMDB21430
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1621954
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20117838
3. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.
4. 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. doi: 10.1073/pnas.81.3.722.
5. Milman HA, Muth R, Cooney DA: Aminomalonic acid and its congeners as potential in vivo inhibitors of L-asparagine synthetase. Enzyme. 1979;24(1):36-47. doi: 10.1159/000458626.
6. Xu MY, Wang P, Sun YJ, Yang L, Wu YJ: Identification of metabolite biomarkers in serum of rats exposed to chlorpyrifos and cadmium. Sci Rep. 2020 Mar 19;10(1):4999. doi: 10.1038/s41598-020-61982-4.
7. Chen JJ, Bai SJ, Li WW, Zhou CJ, Zheng P, Fang L, Wang HY, Liu YY, Xie P: Urinary biomarker panel for diagnosing patients with depression and anxiety disorders. Transl Psychiatry. 2018 Sep 19;8(1):192. doi: 10.1038/s41398-018-0245-0.
8. Xue R, Lin Z, Deng C, Dong L, Liu T, Wang J, Shen X: A serum metabolomic investigation on hepatocellular carcinoma patients by chemical derivatization followed by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2008 Oct;22(19):3061-8. doi: 10.1002/rcm.3708.
9. Matthew, Margaret; Neuberger, A. Aminomalonate. I.U.B. (Intern. Union Biochem.) Symp. Ser. (1963), Volume Date 1962, 30 243-51.
10. 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.
11. 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.
12. Milman HA, Muth R, Cooney DA: Aminomalonic acid and its congeners as potential in vivo inhibitors of L-asparagine synthetase. Enzyme. 1979;24(1):36-47. doi: 10.1159/000458626.
13. Xu MY, Wang P, Sun YJ, Yang L, Wu YJ: Identification of metabolite biomarkers in serum of rats exposed to chlorpyrifos and cadmium. Sci Rep. 2020 Mar 19;10(1):4999. doi: 10.1038/s41598-020-61982-4.
14. Chen JJ, Bai SJ, Li WW, Zhou CJ, Zheng P, Fang L, Wang HY, Liu YY, Xie P: Urinary biomarker panel for diagnosing patients with depression and anxiety disorders. Transl Psychiatry. 2018 Sep 19;8(1):192. doi: 10.1038/s41398-018-0245-0.
15. Xue R, Lin Z, Deng C, Dong L, Liu T, Wang J, Shen X: A serum metabolomic investigation on hepatocellular carcinoma patients by chemical derivatization followed by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2008 Oct;22(19):3061-8. doi: 10.1002/rcm.3708.