Showing metabocard for Aminomalonic acid (BMDB0001147)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:41:41 UTC
Update Date2021-01-12 22:02:00 UTC
BMDB IDBMDB0001147
Secondary Accession Numbers
  • BMDB01147
Metabolite Identification
Common NameAminomalonic acid
DescriptionAminomalonic acid (Ama) is an amino dicarboxylic acid that is an analog of malonic acid in which one of the methylene hydrogens has been replaced by an amino group. It is a strongly acidic compound that is very water soluble. Aminomalonic acid is a natural occurring, largely non-proteogenic amino acid that was first detected in alkaline hydrolysates of proteins in 1984.  Aminomalonic acid is a relatively unstable, minor amino acid in complex structures such as bacteria or tissues. The presence of aminomalonic acid has important biological implications because the malonic acid moiety potentially imparts calcium binding properties to proteins. Possible origins of aminomalonic acid in proteins include its introduction via errors in protein synthesis and oxidative damage to amino acid residues in proteins. (PMID: 1621954 , 6366787 ). Aminomalonic acid can be generated naturally via the activity of mammalian and bacterial enzymes on various precursors such as 2-aminomalonamide, diethylaminomalonate and ketomalonic acid (PMID: 35346 ). Free aminomalonic acid appears to be an oxidation product arising from perturbed serine or threonine metabolism. Aminomalonic acid is produced in animals that have been exposed to Cadmium (a strong pro-oxidant) for extended periods of time and it has been proposed to be a potential biomarker of Cadmium toxicity (PMID: 32193438 ). Aminomalonic acid has also been found to be elevated in the urine of individuals with anxiety and major depressive disorders (PMID: 30232320 ).  Aminomalonic acid has been reported to be a potential biomarker for hepatocellular carcinoma (PMID: 18767022 ) and it exhibits strong inhibitory effects on L-asparagine synthase (PMID: 35346 ). Several metabolomics studies have also found that altered aminomalonic acid levels in serum are associated with neuropsychiatric disorders, melanoma, ketamine overdose and aortic aneurysm, indicating that aminomalonic acid is an important serum indicator for diseases and toxicities (PMID: 32193438 ).
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 Weight119.0761
Monoisotopic Molecular Weight119.021857653
IUPAC Name2-aminopropanedioic acid
Traditional Nameaminomalonic acid
CAS Registry Number1068-84-4
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 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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-2910000000-56ddccdbe51afd85dd6cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2910000000-56ddccdbe51afd85dd6cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0012-1920000000-706a1afd4a87657ef924View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-9200000000-a92a1873b06d13a3cb1bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-7910000000-820eb39fc624884c77c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05i0-9000000000-6da4c50b66acac061cd8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-081c80e5b8aaa8f7ba34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00fr-9000000000-4dbbb4215703aa499e1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-8900000000-ce915814c1e82c9da3e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-c4dc8ccb28224391491fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-dda49c2194c794dfeebbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-b31a9403ea30555205e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-5900000000-8f53ff3974857296fab8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-179c8f28fed467f08059View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9200000000-2cbb45bb0d131a8a5a4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-6bf2575f705bcef140f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-1f92eb692a3016f51886View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-2c6e9d09fa238ac1618cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9400000000-ce7be9ee668d87a767bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9000000000-a28af5b62f46a4285ac2View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Liver
  • Mammary Gland
  • Milk
  • Ruminal Fluid
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis		 details
HMDB IDHMDB0001147
DrugBank IDDB02289
Phenol Explorer Compound IDNot Available
FooDB IDFDB022451
KNApSAcK IDNot Available
Chemspider ID90998
KEGG Compound IDC00872
BioCyc IDAMINOMALONATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound100714
PDB IDNot Available
ChEBI ID17475
References
Synthesis ReferenceMatthew, 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. 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. [PubMed:29197344 ]
  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. doi: 10.1073/pnas.81.3.722. [PubMed:6366787 ]
  3. 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. [PubMed:35346 ]
  4. 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. [PubMed:32193438 ]
  5. 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. [PubMed:30232320 ]
  6. 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. [PubMed:18767022 ]