Record Information |
---|
Version | 5.0 |
---|
Status | Detected but not Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2023-02-21 17:15:29 UTC |
---|
HMDB ID | HMDB0001147 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Aminomalonic acid |
---|
Description | Aminomalonic acid (Ama) is an amino dicarboxylic acid that is an analog of malonic acid in which one of the methylene hydrogens has been replaced by an amino group.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. In particular, aminomalonic acid was isolated from proteins isolated from Escherichia coli cultures and from human atherosclerotic plaques (PMID: 6366787 ). 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 | InChI=1S/C3H5NO4/c4-1(2(5)6)3(7)8/h1H,4H2,(H,5,6)(H,7,8) |
---|
Synonyms | Value | Source |
---|
2-Aminomalonic acid | ChEBI | Aminomalonate | ChEBI | 2-Aminomalonate | Generator | a-Aminomalonic acid | HMDB | alpha-Aminomalonic acid | HMDB | amino-Malonic acid | HMDB | amino-Propanedioate | HMDB | amino-Propanedioic acid | HMDB | Aminopropanedioate | HMDB | Aminopropanedioic acid | HMDB |
|
---|
Chemical Formula | C3H5NO4 |
---|
Average Molecular Weight | 119.0761 |
---|
Monoisotopic Molecular Weight | 119.021857653 |
---|
IUPAC Name | 2-aminopropanedioic acid |
---|
Traditional Name | aminomalonic 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 |
---|
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). |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | Alpha 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 Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular 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 |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Aminomalonic acid,1TMS,isomer #1 | C[Si](C)(C)OC(=O)C(N)C(=O)O | 1257.1 | Semi standard non polar | 33892256 | Aminomalonic acid,1TMS,isomer #2 | C[Si](C)(C)NC(C(=O)O)C(=O)O | 1325.4 | Semi standard non polar | 33892256 | Aminomalonic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(N)C(=O)O[Si](C)(C)C | 1308.9 | Semi standard non polar | 33892256 | Aminomalonic acid,2TMS,isomer #2 | C[Si](C)(C)NC(C(=O)O)C(=O)O[Si](C)(C)C | 1376.8 | Semi standard non polar | 33892256 | Aminomalonic acid,2TMS,isomer #3 | C[Si](C)(C)N(C(C(=O)O)C(=O)O)[Si](C)(C)C | 1549.6 | Semi standard non polar | 33892256 | Aminomalonic acid,3TMS,isomer #1 | C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1463.6 | Semi standard non polar | 33892256 | Aminomalonic acid,3TMS,isomer #1 | C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1427.9 | Standard non polar | 33892256 | Aminomalonic acid,3TMS,isomer #1 | C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1566.2 | Standard polar | 33892256 | Aminomalonic acid,3TMS,isomer #2 | C[Si](C)(C)OC(=O)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1557.9 | Semi standard non polar | 33892256 | Aminomalonic acid,3TMS,isomer #2 | C[Si](C)(C)OC(=O)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1460.0 | Standard non polar | 33892256 | Aminomalonic acid,3TMS,isomer #2 | C[Si](C)(C)OC(=O)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1679.8 | Standard polar | 33892256 | Aminomalonic acid,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1639.0 | Semi standard non polar | 33892256 | Aminomalonic acid,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1547.6 | Standard non polar | 33892256 | Aminomalonic acid,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1543.9 | Standard polar | 33892256 | Aminomalonic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(N)C(=O)O | 1508.4 | Semi standard non polar | 33892256 | Aminomalonic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(C(=O)O)C(=O)O | 1603.4 | Semi standard non polar | 33892256 | Aminomalonic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(N)C(=O)O[Si](C)(C)C(C)(C)C | 1735.8 | Semi standard non polar | 33892256 | Aminomalonic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C | 1804.6 | Semi standard non polar | 33892256 | Aminomalonic acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(C(C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C | 1951.1 | Semi standard non polar | 33892256 | Aminomalonic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2055.8 | Semi standard non polar | 33892256 | Aminomalonic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2044.3 | Standard non polar | 33892256 | Aminomalonic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1996.8 | Standard polar | 33892256 | Aminomalonic acid,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2173.2 | Semi standard non polar | 33892256 | Aminomalonic acid,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2098.5 | Standard non polar | 33892256 | Aminomalonic acid,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2035.9 | Standard polar | 33892256 | Aminomalonic acid,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2415.3 | Semi standard non polar | 33892256 | Aminomalonic acid,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2345.1 | Standard non polar | 33892256 | Aminomalonic acid,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2068.5 | Standard polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental GC-MS | GC-MS Spectrum - Aminomalonic acid GC-MS (2 TMS) | splash10-001i-2910000000-56ddccdbe51afd85dd6c | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Aminomalonic acid GC-MS (3 TMS) | splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Aminomalonic acid GC-MS (Non-derivatized) | splash10-001i-2910000000-56ddccdbe51afd85dd6c | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Aminomalonic acid GC-MS (Non-derivatized) | splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Aminomalonic acid GC-EI-TOF (Non-derivatized) | splash10-0012-1920000000-706a1afd4a87657ef924 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Aminomalonic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00xu-9200000000-a92a1873b06d13a3cb1b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Aminomalonic acid GC-MS (2 TMS) - 70eV, Positive | splash10-006t-7910000000-820eb39fc624884c77c9 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Aminomalonic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminomalonic acid 20V, Positive-QTOF | splash10-05i0-9000000000-6da4c50b66acac061cd8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminomalonic acid 40V, Positive-QTOF | splash10-0a4i-9000000000-081c80e5b8aaa8f7ba34 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminomalonic acid 10V, Positive-QTOF | splash10-00fr-9000000000-4dbbb4215703aa499e1b | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 10V, Positive-QTOF | splash10-00di-8900000000-ce915814c1e82c9da3e2 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 20V, Positive-QTOF | splash10-00di-9200000000-c4dc8ccb28224391491f | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 40V, Positive-QTOF | splash10-056r-9000000000-dda49c2194c794dfeebb | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 10V, Negative-QTOF | splash10-014i-2900000000-b31a9403ea30555205e6 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 20V, Negative-QTOF | splash10-01b9-5900000000-8f53ff3974857296fab8 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 40V, Negative-QTOF | splash10-00di-9000000000-179c8f28fed467f08059 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 10V, Positive-QTOF | splash10-00di-9200000000-2cbb45bb0d131a8a5a4c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 20V, Positive-QTOF | splash10-00di-9000000000-6bf2575f705bcef140f5 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 40V, Positive-QTOF | splash10-0a4i-9000000000-1f92eb692a3016f51886 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 10V, Negative-QTOF | splash10-014i-3900000000-2c6e9d09fa238ac1618c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 20V, Negative-QTOF | splash10-00di-9400000000-ce7be9ee668d87a767bd | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminomalonic acid 40V, Negative-QTOF | splash10-00dl-9000000000-a28af5b62f46a4285ac2 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
|
---|
General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
|
---|