ECMDB: 2-Aminoacrylic acid (ECMDB03609) (M2MDB000519)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (11)XML

Proteins (429)

Record Information

Version

2.0

Creation Date

2012-05-31 14:00:04 -0600

Update Date

2015-07-07 11:03:13 -0600

Secondary Accession Numbers

ECMDB03609

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 3D-SDF PDB SMILES InChI View 3D 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

Weight:

Average: 87.0773
Monoisotopic: 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

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
Amino acid
Carboxylic acid
Enamine
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:17123 )
enamine (CHEBI:17123 )
alpha,beta-unsaturated monocarboxylic acid (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 g/L	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:

SMPDB Pathways:

D-serine degradation	PW002101
Nitrogen metabolism	PW000755
Sulfur metabolism	PW000922
Tryptophan metabolism	PW000815
Uracil degradation III	PW002026
serine biosynthesis and metabolism	PW000809
sulfur metabolism (butanesulfonate)	PW000923
sulfur metabolism (butanesulfonate/phenylacetaldehyde)	PW001012
sulfur metabolism (ethanesulfonate)	PW000925
sulfur metabolism (isethionate)	PW000926
sulfur metabolism (methanesulfonate)	PW000927
sulfur metabolism (propanesulfonate)	PW000924
tryptophan metabolism II	PW001916

KEGG Pathways:

Cysteine and methionine metabolism ec00270
Glycine, serine and threonine metabolism ec00260
Metabolic pathways eco01100
Nitrogen metabolism ec00910
Selenoamino acid metabolism ec00450
Sulfur metabolism ec00920
Tryptophan metabolism ec00380

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	splash10-0006-9000000000-91e0ae8251c533ccb7ad	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9500000000-d9a0c6188aef6b8aec5a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-ff7f2c935a022bb6caf6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-ff7f2c935a022bb6caf6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ff7f2c935a022bb6caf6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-cb7bf9d7a9fec42be16c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-56882758237b475e8194	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f6f1fa2beae1e80da0d0	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:

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

Enzymes

Protein Details

1. D-serine dehydratase

General function:: Involved in D-serine ammonia-lyase activity
Specific function:: D-serine = pyruvate + NH(3)
Gene Name:: dsdA
Uniprot ID:: P00926
Molecular weight:: 47900

Reactions

D-serine = pyruvate + NH(3).

Protein Details

2. Cystathionine beta-lyase metC

General function:: Involved in pyridoxal phosphate binding
Specific function:: L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate
Gene Name:: metC
Uniprot ID:: P06721
Molecular weight:: 43212

Reactions

L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate.

Protein Details

3. Tryptophanase

General function:: Involved in lyase activity
Specific function:: L-tryptophan + H(2)O = indole + pyruvate + NH(3)
Gene Name:: tnaA
Uniprot ID:: P0A853
Molecular weight:: 52773

Reactions

L-tryptophan + H(2)O = indole + pyruvate + NH(3).

Protein Details

4. Cysteine synthase A

General function:: Involved in cysteine biosynthetic process from serine
Specific function:: O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:: cysK
Uniprot ID:: P0ABK5
Molecular weight:: 34489

Reactions

O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
3-chloro-L-alanine + thioglycolate = S-carboxymethyl-L-cysteine + chloride.

Protein Details

5. L-serine dehydratase 1

General function:: Involved in L-serine ammonia-lyase activity
Specific function:: Deaminates also threonine, particularly when it is present in high concentration
Gene Name:: sdaA
Uniprot ID:: P16095
Molecular weight:: 48906

Reactions

L-serine = pyruvate + NH(3).

Protein Details

6. Cysteine synthase B

General function:: Involved in cysteine biosynthetic process from serine
Specific function:: Two cysteine synthase enzymes are found. Both catalyze the same reaction. Cysteine synthase B can also use thiosulfate in place of sulfide to give cysteine thiosulfonate as a product
Gene Name:: cysM
Uniprot ID:: P16703
Molecular weight:: 32664

Reactions

O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.

Protein Details

7. Protein malY

General function:: Involved in transferase activity
Specific function:: Acts as a beta-cystathionase and as a repressor of the maltose regulon
Gene Name:: malY
Uniprot ID:: P23256
Molecular weight:: 43641

Reactions

L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate.

Protein Details

8. L-serine dehydratase 2

General function:: Involved in L-serine ammonia-lyase activity
Specific function:: Deaminates also threonine, particularly when it is present in high concentration
Gene Name:: sdaB
Uniprot ID:: P30744
Molecular weight:: 48753

Reactions

L-serine = pyruvate + NH(3).

Protein Details

9. L-serine dehydratase tdcG

General function:: Involved in L-serine ammonia-lyase activity
Specific function:: L-serine = pyruvate + NH(3)
Gene Name:: tdcG
Uniprot ID:: P42630
Molecular weight:: 48521

Reactions

L-serine = pyruvate + NH(3).

Protein Details

10. UPF0076 protein rutC

General function:: Translation, ribosomal structure and biogenesis
Specific function:: Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutC
Uniprot ID:: P0AFQ5
Molecular weight:: 13763

Protein Details

11. Protein rutD

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:: Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutD
Uniprot ID:: P75895
Molecular weight:: 28898

Reactions

(Z)-3-aminoacrylate + H(2)O = malonate semialdehyde + NH(3).

2-Aminoacrylic acid (ECMDB03609) (M2MDB000519)

Structure for #<Compound:0xa83c09bc>

Enzymes

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