1.0 2016-09-30 22:41:41 UTC 2021-01-12 22:02:00 UTC BMDB0001147 BMDB01147 Aminomalonic acid 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acid (Ama) is an amino dicarboxylic acid that is an analog of malonic acid in which one of the methylene hydrogens has been replaced by an amino group.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.  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). 2-Aminomalonic acid Aminomalonate 2-Aminomalonate a-Aminomalonic acid alpha-Aminomalonic acid amino-Malonic acid amino-Propanedioate amino-Propanedioic acid Aminopropanedioate Aminopropanedioic acid C3H5NO4 119.0761 119.021857653 2-aminopropanedioic acid aminomalonic acid 1068-84-4 NC(C(O)=O)C(O)=O InChI=1S/C3H5NO4/c4-1(2(5)6)3(7)8/h1H,4H2,(H,5,6)(H,7,8) JINBYESILADKFW-UHFFFAOYSA-N 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). Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Alpha amino acids 1,3-dicarbonyl compounds Amino acids Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds 1,3-dicarbonyl compound Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Aliphatic acyclic compounds amino dicarboxylic acid Solid logp -3.50 ALOGPS logs 0.03 ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 0.45 ChemAxon pka_strongest_basic 8.5 ChemAxon iupac 2-aminopropanedioic acid ChemAxon average_mass 119.0761 ChemAxon mono_mass 119.021857653 ChemAxon smiles NC(C(O)=O)C(O)=O ChemAxon formula C3H5NO4 ChemAxon inchi InChI=1S/C3H5NO4/c4-1(2(5)6)3(7)8/h1H,4H2,(H,5,6)(H,7,8) ChemAxon inchikey JINBYESILADKFW-UHFFFAOYSA-N ChemAxon polar_surface_area 100.62 ChemAxon refractivity 21.98 ChemAxon polarizability 9.48 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsIr 1100 Specdb::MsIr 1101 Specdb::MsIr 1102 Specdb::MsMs 27068 Specdb::MsMs 27069 Specdb::MsMs 27070 Specdb::MsMs 33626 Specdb::MsMs 33627 Specdb::MsMs 33628 Specdb::MsMs 2226262 Specdb::MsMs 2228661 Specdb::MsMs 2230766 Specdb::MsMs 2664256 Specdb::MsMs 2664257 Specdb::MsMs 2664258 Specdb::MsMs 3017607 Specdb::MsMs 3017608 Specdb::MsMs 3017609 Specdb::NmrOneD 146610 Specdb::NmrOneD 146611 Specdb::NmrOneD 146612 Specdb::NmrOneD 146613 Specdb::NmrOneD 146614 Specdb::NmrOneD 146615 Specdb::NmrOneD 146616 Specdb::NmrOneD 146617 Specdb::NmrOneD 146618 Specdb::NmrOneD 146619 Specdb::NmrOneD 146620 Specdb::NmrOneD 146621 Specdb::NmrOneD 146622 Specdb::NmrOneD 146623 Specdb::NmrOneD 146624 Specdb::NmrOneD 146625 Specdb::NmrOneD 146626 Specdb::NmrOneD 146627 Specdb::NmrOneD 146628 Specdb::NmrOneD 146629 Specdb::CMs 1033 Specdb::CMs 1107 Specdb::CMs 22533 Specdb::CMs 31279 Specdb::CMs 31280 Specdb::CMs 32362 Specdb::CMs 37947 Specdb::CMs 158171 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Raw milk, by GC-TOF/MS 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. 29197344 Ruminal Fluid Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Semen Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was identified by probable match parameters of the NIST Mass Spectral Search Program Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018. 29634739 C00872 DB02289 FDB022451 90998 17475 100714 AMINOMALONATE Matthew, Margaret; Neuberger, A. Aminomalonate. I.U.B. (Intern. Union Biochem.) Symp. Ser. (1963), Volume Date 1962, 30 243-51. 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. 29197344 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. 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. 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. 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. 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. 18767022