ChemFOnt: Showing chemical card for Aminomalonic acid (CFc000000893)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:24 UTC

Chemfont ID

CFc000000893

Molecule Identification

Common Name

Aminomalonic acid

Definition

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acid (Ama) is an amino dicarboxylic acid that is an analog of malonic acid in which one of the methylene hydrogens has been replaced by an amino group.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

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 )

Functional Ontology

Not Available

Urine (PMID: 24023812)
Feces (PMID: 20669995)
Sweat (PMID: 26755145)

Source

Exogenous

Exogenous (HMDB: HMDB0001147)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0001147)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Threonine Biosynthesis (PathBank: SMP0121292)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001147)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	126 g/L	ALOGPS
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon