Record Information
Version2.0
Creation Date2015-09-08 17:50:03 -0600
Update Date2015-09-14 16:46:32 -0600
Secondary Accession Numbers
  • ECMDB24204
Identification
Name: (2Z)-2-aminobut-2-enoate
Description(2Z)-2-aminobut-2-enoate is an intermediate of pathways L-threonine degradation I and L-isoleucine biosynthesis I in E. coli. It is a product for enzymes threonine dehydratase and threonine deaminase which catalyze the reaction L-threonine -> (2Z)-2-aminobut-2-enoate + H2O + H+ in both pathways. (2Z)-2-aminobut-2-enoate is also a substrate of the spontaneous reaction (2Z)-2-aminobut-2-enoate -> 2-iminobutanoate in both pathways (BioCyc compound: CPD-15056).
Structure
Thumb
Synonyms:
  • (2Z)-2-Aminobut-2-enoic acid
Chemical Formula:C4H6NO2
Weight:Average: 100.098
Monoisotopic: 100.040402017
InChI Key:PAWSVPVNIXFKOS-UHFFFAOYSA-M
InChI:InChI=1S/C4H7NO2/c1-2-3(5)4(6)7/h2H,5H2,1H3,(H,6,7)/p-1
CAS number:Not Available
IUPAC Name:2-aminobut-2-enoate
Traditional IUPAC Name:2-aminobut-2-enoate
SMILES:CC=C(N)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
  • Unsaturated fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Enamine
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility331 g/LALOGPS
logP0.14ALOGPS
logP-2.5ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)2.88ChemAxon
pKa (Strongest Basic)8.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.43 m³·mol⁻¹ChemAxon
Polarizability9.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
isoleucine biosynthesisPW000818 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-6ed497c330d9eed7826aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9400000000-ae6c0445953831ec5db5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adu-9000000000-0a340f500e7c3b2a3aa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-81e5188ad5ef965cdcebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-59e7d5fa2a54f1b934e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9000000000-38c6929979cd032608eeView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID58739
HMDB IDNot Available
Pubchem Compound ID75104761
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the formation of alpha-ketobutyrate from threonine in a two-step reaction. The first step is a dehydration of threonine, followed by rehydration and liberation of ammonia. Deaminates L-threonine, but also L-serine to a lesser extent
Gene Name:
ilvA
Uniprot ID:
P04968
Molecular weight:
56195
Reactions
L-threonine = 2-oxobutanoate + NH(3).