Milk Composition Database: Showing metabocard for Aminomalonic acid (BMDB0001147)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:41:41 UTC

Update Date

2021-01-12 22:02:00 UTC

MCDB ID

BMDB0001147

Secondary Accession Numbers

BMDB01147

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acid (Ama) is an amino dicarboxylic acid that is an analog of malonic acid in which one of the methylene hydrogens has been replaced by an amino group.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. 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

MOL SDF PDB SMILES InChI

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

amino dicarboxylic acid (CHEBI:17475 )

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
logP	-3.5	ALOGPS
logP	-3.4	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	0.45	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	21.98 m³·mol⁻¹	ChemAxon
Polarizability	9.48 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-2910000000-56ddccdbe51afd85dd6c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-2910000000-56ddccdbe51afd85dd6c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0012-1920000000-706a1afd4a87657ef924	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xu-9200000000-a92a1873b06d13a3cb1b	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006t-7910000000-820eb39fc624884c77c9	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05i0-9000000000-6da4c50b66acac061cd8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-081c80e5b8aaa8f7ba34	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-9000000000-4dbbb4215703aa499e1b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-8900000000-ce915814c1e82c9da3e2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9200000000-c4dc8ccb28224391491f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-dda49c2194c794dfeebb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-b31a9403ea30555205e6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-5900000000-8f53ff3974857296fab8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-179c8f28fed467f08059	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9200000000-2cbb45bb0d131a8a5a4c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-6bf2575f705bcef140f5	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-1f92eb692a3016f51886	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-2c6e9d09fa238ac1618c	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9400000000-ce7be9ee668d87a767bd	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-a28af5b62f46a4285ac2	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29197344	details

External Links

HMDB ID

HMDB0001147

DrugBank ID

DB02289

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022451

KNApSAcK ID

Not Available

Chemspider ID

90998

KEGG Compound ID

C00872

BioCyc ID

AMINOMALONATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100714

PDB ID

Not Available

ChEBI ID

17475

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

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 ]
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 ]
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 ]

Showing metabocard for Aminomalonic acid (BMDB0001147)

Structure for BMDB0001147 (Aminomalonic acid)