Record Information
Version2.0
Creation Date2015-06-04 15:12:11 -0600
Update Date2015-08-05 16:22:04 -0600
Secondary Accession Numbers
  • ECMDB23740
Identification
Name:2-Aminobut-2-enoate
Description:Conjugate base of 2-aminobut-2-enoic acid
Structure
Thumb
Synonyms:
  • (2Z)-2-Aminobut-2-enoate
  • (2Z)-2-Aminobut-2-enoic acid
  • (Z)-2-Aminobutenoate
  • (Z)-2-Aminobutenoic acid
  • (Z)-Dehydrobutyrine
  • (Z)2,3-Didehydrobutyrine
  • 2-Aminobut-2-enoic acid
  • 2-Ammoniobut-2-enoate
  • 2-Ammoniobut-2-enoic acid
  • a,b-Dehydroaminobutyrate
  • a,b-Dehydroaminobutyric acid
  • alpha,beta-Dehydroaminobutyrate
  • alpha,beta-Dehydroaminobutyric acid
  • Anhydrothreonine
  • α,β-dehydroaminobutyrate
  • α,β-dehydroaminobutyric acid
Chemical Formula:C4H7NO2
Weight:Average: 101.1039
Monoisotopic: 101.047678473
InChI Key:PAWSVPVNIXFKOS-IHWYPQMZSA-N
InChI:InChI=1S/C4H7NO2/c1-2-3(5)4(6)7/h2H,5H2,1H3,(H,6,7)/b3-2-
CAS number:71018-10-5
IUPAC Name:(2Z)-2-aminobut-2-enoic acid
Traditional IUPAC Name:Z-dehydrobutyrine
SMILES:C\C=C(/N)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Unsaturated fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Enamine
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility188 g/LALOGPS
logP0.26ALOGPS
logP-2.5ChemAxon
logS0.27ALOGPS
pKa (Strongest Acidic)2.88ChemAxon
pKa (Strongest Basic)8.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.59 m³·mol⁻¹ChemAxon
Polarizability9.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Glycine, serine and threonine metabolism ec00260
  • Metabolic pathways eco01100
  • Valine, leucine and isoleucine biosynthesis ec00290
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-9200000000-c0316113ab7015d6e1f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-54a3fe3b45654f66a2c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8d871dc458743ae66dc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4900000000-dc956c23c91dd13ef355View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-9500000000-580439f60c052759d0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-9000000000-7182f1e4996b02cd2950View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18820
HMDB IDNot Available
Pubchem Compound ID6449989
Kegg IDC17234
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).
General function:
Involved in catalytic activity
Specific function:
Acts on both serine and threonine, and properly considered as a hydroxy amino acid deaminase
Gene Name:
tdcB
Uniprot ID:
P0AGF6
Molecular weight:
35232
Reactions
L-threonine = 2-oxobutanoate + NH(3).
L-serine = pyruvate + NH(3).