Livestock Metabolome Database: Showing metabocard for Aminomalonic acid (LMDB00301)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:49 UTC

Update Date

2016-09-23 18:45:06 UTC

Lmdb

LMDB00301

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Aminomalonic acid

Description

Aminomalonic acid (Ama) was first detected in alkaline hydrolysates of proteins in 1984. Ama has been isolated from proteins of Escherichia coli and animal atherosclerotic plaque. The presence of Ama has important biological implications because the malonic acid moiety potentially imparts calcium binding properties to protein. Ama is not formed from any of the 20 major amino acids during the hydrolysis procedure. Furthermore, the amount of Ama found does not depend on the presence of small amounts of O2 during the hydrolysis. No artifactual formation of ama has been demonstrated and may indeed be a constituent of proteins before the hydrolysis procedure. Possible origins of Ama include errors in protein synthesis and oxidative damage to amino acid residues in proteins. (PMID: 1621954 , 6366787 ).

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-2910000000-56ddccdbe51afd85dd6c	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-2910000000-56ddccdbe51afd85dd6c	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-1790000000-1a2cf2f982d08de4d2c9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0012-1920000000-706a1afd4a87657ef924	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xu-9200000000-a92a1873b06d13a3cb1b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006t-7910000000-820eb39fc624884c77c9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05i0-9000000000-6da4c50b66acac061cd8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-081c80e5b8aaa8f7ba34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-9000000000-4dbbb4215703aa499e1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-8900000000-ce915814c1e82c9da3e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9200000000-c4dc8ccb28224391491f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-dda49c2194c794dfeebb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-b31a9403ea30555205e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-5900000000-8f53ff3974857296fab8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-179c8f28fed467f08059	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9200000000-2cbb45bb0d131a8a5a4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-6bf2575f705bcef140f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-1f92eb692a3016f51886	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-2c6e9d09fa238ac1618c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9400000000-ce7be9ee668d87a767bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-a28af5b62f46a4285ac2	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Cerebrospinal Fluid (CSF)
Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Applicable	Not Available	Ovine	17510975	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22675387	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23255817	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	22761248	details

External Links

DrugBank ID

DB02289

HMDB ID

HMDB0001147

FooDB ID

FDB022451

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

AMINOMALONATE

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB21430

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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. [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. [6366787 ]

Showing metabocard for Aminomalonic acid (LMDB00301)

Structure for LMDB00301 (Aminomalonic acid)