Record Information
Version2.0
Creation Date2012-05-31 14:00:04 -0600
Update Date2015-07-07 11:03:13 -0600
Secondary Accession Numbers
  • ECMDB03609
Identification
Name:2-Aminoacrylic acid
DescriptionDehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid).
Structure
Thumb
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.651PhysProp
Predicted Properties
PropertyValueSource
Water Solubility233 g/LALOGPS
logP-0.13ALOGPS
logP-2.9ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)2.58ChemAxon
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.92 m³·mol⁻¹ChemAxon
Polarizability7.72 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
D-serine degradationPW002101 ThumbThumb?image type=greyscaleThumb?image type=simple
Nitrogen metabolismPW000755 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
Uracil degradation IIIPW002026 ThumbThumb?image type=greyscaleThumb?image type=simple
serine biosynthesis and metabolismPW000809 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (butanesulfonate)PW000923 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (butanesulfonate/phenylacetaldehyde)PW001012 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (ethanesulfonate)PW000925 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (isethionate)PW000926 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (methanesulfonate)PW000927 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (propanesulfonate)PW000924 ThumbThumb?image type=greyscaleThumb?image type=simple
tryptophan metabolism IIPW001916 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-91e0ae8251c533ccb7adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9500000000-d9a0c6188aef6b8aec5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9000000000-15dc8dc52e98be913462View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-dc312ec6c67a0557dea5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6abf262be2b6f2447777View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-8d7c53619f483f86f61aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-e78e6283f6f0fd640c07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-9000000000-f45341969a54a57e8b77View 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
External Links:
ResourceLink
CHEBI ID17123
HMDB IDHMDB03609
Pubchem Compound ID123991
Kegg IDC02218
ChemSpider ID110510
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoDHA

Enzymes

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).
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.
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).
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.
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).
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.
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.
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).
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).
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
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).