P. aeruginosa Metabolome Database: 2-Aminoacrylic acid (PAMDB000519)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000519

Identification

Name:

2-Aminoacrylic acid

Description:

Dehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(a)-(b)-Di-dehydroalanine
(alpha)-(beta)-di-dehydroalanine
(α)-(β)-Di-dehydroalanine
2-Aminoacrylate
2-Aminoacrylic acid
A-b-Di-dehydroalanine
Alpha-beta-Di-dehydroalanine
Dehydroalanine
α-β-Di-dehydroalanine

Chemical Formula:

C₃H₅NO₂

Average Molecular Weight:

87.0773

Monoisotopic Molecular Weight:

87.032028409

InChI Key:

UQBOJOOOTLPNST-UHFFFAOYSA-N

InChI:

InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6)

CAS number:

Not Available

IUPAC Name:

2-aminoprop-2-enoic acid

Traditional IUPAC Name:

dehydroalanine

SMILES:

NC(=C)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound 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
Monocarboxylic acid or derivatives
Enamine
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enamine (CHEBI:17123 )
alpha-amino acid (CHEBI:17123 )
alpha,beta-unsaturated monocarboxylic acid (CHEBI:17123 )
alanine derivative (CHEBI:17123 )
dehydroamino acid (CHEBI:17123 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-2.651	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	233.0 mg/mL	ALOGPS
logP	-0.13	ALOGPS
logP	-2.9	ChemAxon
logS	0.43	ALOGPS
pKa (Strongest Acidic)	2.58	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	20.92 m³·mol^-1	ChemAxon
Polarizability	7.72 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:

L-Serine <> 2-Aminoacrylic acid + Water
L-Cystathionine + Water + 2-Aminoacrylic acid + 2-Iminopropanoate <> L-Homocysteine + Pyruvic acid + Ammonia
L-Serine + 2-Aminoacrylic acid + 2-Iminopropanoate + Water <> Pyruvic acid + Ammonia
D-Serine + 2-Aminoacrylic acid + 2-Iminopropanoate + Water <> Pyruvic acid + Ammonia
L-Tryptophan + Water + 2-Aminoacrylic acid + 2-Iminopropanoate <> Indole + Pyruvic acid + Ammonia
L-Cysteine > Hydrogen ion + Hydrogen sulfide + 2-Aminoacrylic acid
L-Tryptophan > Hydrogen ion + Indole + 2-Aminoacrylic acid
L-Serine + L-Serine > Water + Hydrogen ion + 2-Aminoacrylic acid

Pathways:

Cysteine and methionine metabolism pae00270
Glycine, serine and threonine metabolism pae00260
Metabolic pathways pae01100
Nitrogen metabolism pae00910
Selenoamino acid metabolism pae00450
Sulfur metabolism pae00920
Tryptophan metabolism pae00380

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9000000000-15dc8dc52e98be913462	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-dc312ec6c67a0557dea5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-6abf262be2b6f2447777	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-8d7c53619f483f86f61a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-e78e6283f6f0fd640c07	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-9000000000-f45341969a54a57e8b77	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17123
HMDB ID	HMDB03609
Pubchem Compound ID	123991
Kegg ID	C02218
ChemSpider ID	110510
Wikipedia ID	Not Available
BioCyc ID	Not Available
Ligand Expo	DHA

2-Aminoacrylic acid (PAMDB000519)

Structure for 2-Aminoacrylic acid (PAMDB000519)