ECMDB: 2-Aminomalonate semialdehyde (ECMDB21153) (M2MDB001562)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (1)

Record Information

Version

2.0

Creation Date

2012-07-30 14:54:42 -0600

Update Date

2015-06-03 17:20:45 -0600

Secondary Accession Numbers

ECMDB21153

Identification

Name:

2-Aminomalonate semialdehyde

Description

2-Aminomalonate semialdehyde is an organic compound that can be formed from a reaction between NADP+ and L-serine. (EcoCyc)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2S)-2-amino-3-oxopropanoate
(2S)-2-amino-3-oxopropanoic acid
(S)-2-amino-3-oxopropanoate
(S)-2-amino-3-oxopropanoic acid
2-Amino-3-oxo-Propanoate
2-Amino-3-oxo-Propanoic acid
2-Amino-3-oxopropionate
2-Amino-3-oxopropionic acid
2-Aminomalonate semialdehyde
2-Aminomalonic acid semialdehyde
2-Ammoniomalonate semialdehyde
2-Ammoniomalonic acid semialdehyde
2-Formylglycine
3-Oxo-(9CI)-Alanine
3-Oxo-L-alanine
3-Oxoalanine
A-Formylglycine
Alpha-Formylglycine
Amino-(8CI)Malonaldehydate
Amino-(8CI)Malonaldehydic acid
L-3-Oxoalanine
L-a-Formylglycine
L-alpha-Formylglycine
L-Amino-malonate semialdehyde
L-Amino-malonic acid semialdehyde
L-Aminomalonaldehydate
L-Aminomalonaldehydic acid
L-Serine semialdehyde [misnomer]
L-α-Formylglycine
α-Formylglycine

Chemical Formula:

C₃H₅NO₃

Weight:

Average: 103.0767
Monoisotopic: 103.026943031

InChI Key:

XMTCKNXTTXDPJX-REOHCLBHSA-N

InChI:

InChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)/t2-/m0/s1

CAS number:

5735-66-0

IUPAC Name:

(2S)-2-amino-3-oxopropanoic acid

Traditional IUPAC Name:

2-aminomalonate semialdehyde

SMILES:

N[C@@H](C=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
1,3-dicarbonyl compound
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Aldehyde
Carbonyl group
Amine
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:37012 )
L-alanine derivative (CHEBI:37012 )
3-oxoalanine (CHEBI:37012 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	242 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-3.6	ChemAxon
logS	0.37	ALOGPS
pKa (Strongest Acidic)	1.66	ChemAxon
pKa (Strongest Basic)	7.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	21.06 m³·mol⁻¹	ChemAxon
Polarizability	8.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

NADP + L-Serine <> 2-Aminomalonate semialdehyde + Hydrogen ion + NADPH
NADP + D-Serine <> 2-Aminomalonate semialdehyde + Hydrogen ion + NADPH
L-Serine + NADP 2-Aminomalonate semialdehyde + NADPH + Hydrogen ion
3-Hydroxyisobutyric acid + NAD <> 2-Aminomalonate semialdehyde + NADH
2-Aminomalonate semialdehyde + NADPH + Hydrogen ion <> NADP + L-Serine

SMPDB Pathways:

Secondary Metabolites: cysteine biosynthesis from serine

PW000977

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-129e33e49404ea4ec543	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k9i-9300000000-1a42eb4f596f6dcd8e32	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-bb288560905cc883049b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-005758ce9275f75a9c80	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-4900000000-32e8e76f27ffbb43d6c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgi-9500000000-c8b763e487f04ffaa17d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-d3736532a9a9202b1aa9	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	58671
HMDB ID	HMDB11602
Pubchem Compound ID	25244138
Kegg ID	C11822
ChemSpider ID	391645
Wikipedia ID	Not Available
BioCyc ID	2-AMINOMALONATE-SEMIALDEHYDE
EcoCyc ID	2-AMINOMALONATE-SEMIALDEHYDE

Enzymes

Protein Details

1. NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADP-dependent oxidation of L-allo- threonine to L-2-amino-3-keto-butyrate, which is spontaneously decarboxylated into aminoacetone. Also acts on L-serine, D-serine, D-threonine, D-3-hydroxyisobutyrate, L-3-hydroxyisobutyrate, D- glycerate and L-glycerate
Gene Name:: ydfG
Uniprot ID:: P39831
Molecular weight:: 27249

Reactions

3-hydroxypropanoate + NADP(+) = 3-oxopropanoate + NADPH.

2-Aminomalonate semialdehyde (ECMDB21153) (M2MDB001562)

Structure for #<Compound:0xa9d839bc>

Enzymes

Reactions