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3-Aminoacrylate (M2MDB001576)

Record Information
Version2.0
Creation Date2012-07-30 14:54:43 -0600
Update Date2015-06-03 17:20:47 -0600
Secondary Accession Numbers
  • ECMDB21167
Identification
Name:3-Aminoacrylate
Description3-aminoacrylate is a member of the chemical class known as Enones. These are compounds containing the enone functional group, with the structure RC(=O)CR'. Aminoacrylate is involved in amino acid metabolism. A new amino acid is formed when the nucleophiles add to the aminoacrylate. (PMID 8663055)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (2Z)-3-aminoprop-2-enoate
  • (2Z)-3-aminoprop-2-enoic acid
  • (Z)-3-Aminoacrylate
  • (Z)-3-Aminoacrylic acid
  • 3-Aminoacrylate
  • 3-Aminoacrylic acid
  • Aminoacrylate
  • Aminoacrylic acid
Chemical Formula:C3H5NO2
Weight:Average: 87.0773
Monoisotopic: 87.032028409
InChI Key:YTLYLLTVENPWFT-UPHRSURJSA-N
InChI:InChI=1S/C3H5NO2/c4-2-1-3(5)6/h1-2H,4H2,(H,5,6)/b2-1-
CAS number:Not Available
IUPAC Name:(2Z)-3-aminoprop-2-enoic acid
Traditional IUPAC Name:aminoacrylic acid
SMILES:N\C=C/C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAcrylic acids and derivatives
Direct ParentAcrylic acids and derivatives
Alternative Parents
Substituents
  • Acrylic acid or derivatives
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Enamine
  • Monocarboxylic acid or derivatives
  • Allylamine
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility293 g/LALOGPS
logP-0.42ALOGPS
logP-2.7ChemAxon
logS0.53ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)6.65ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.93 m³·mol⁻¹ChemAxon
Polarizability7.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-Aminoacrylate + Hydrogen ion + Water > Malonic semialdehyde + Ammonium
NADH + Peroxyaminoacrylate > 3-Aminoacrylate + Water + NAD
Ureidoacrylate + Water <> 3-Aminoacrylate + Carbamic acid
Peroxyaminoacrylate <> 3-Aminoacrylate
3-Aminoacrylate + Water <> Malonic semialdehyde + Ammonia
3-ureidoacrylate + Water > Hydrogen ion + Carbamic acid + 3-Aminoacrylate
3-Aminoacrylate + Water > Malonic semialdehyde + Ammonia
Peroxyaminoacrylate + a reduced electron acceptor > 3-Aminoacrylate + Water + Hydrogen ion + an oxidized electron acceptor
(Z)-3-Ureidoacrylate + Water > 3-Aminoacrylate + Carbon dioxide + Ammonia
3-Aminoacrylate + Water > Malonic acid + Ammonia
Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Carbamic acid + Hydrogen ion + 3-Aminoacrylate
Peroxyaminoacrylate + an unknown reduced electron acceptor + 3-Aminoacrylate > 2-Aminoacrylic acid + an unknown oxidized electron acceptor
SMPDB Pathways:
Uracil degradation IIIPW002026 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-04ede35a7e8ccb1a1583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-90549ba6315b89041625View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-9000000000-2e75d1ab630a49ed5ffdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2e5d7401c27942249cdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-9000000000-78d2bc9572a1c23efcd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-428ecd02d0bf7fc25ac8View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Flint, D. H., Tuminello, J. F., Miller, T. J. (1996). "Studies on the synthesis of the Fe-S cluster of dihydroxy-acid dehydratase in escherichia coli crude extract. Isolation of O-acetylserine sulfhydrylases A and B and beta-cystathionase based on their ability to mobilize sulfur from cysteine and to participate in Fe-S cluster synthesis." J Biol Chem 271:16053-16067. Pubmed: 8663055
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID59894
HMDB IDNot Available
Pubchem Compound ID46173135
Kegg IDC20253
ChemSpider ID26331746
Wikipedia IDNot Available
BioCyc IDCPD0-2339
EcoCyc IDCPD0-2339

Enzymes

Protein Details
1. 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
2. Putative isochorismatase family protein rutB
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:
rutB
Uniprot ID:
P75897
Molecular weight:
25209
Reactions
(Z)-3-ureidoacrylate peracid + H(2)O = (Z)-3-peroxyaminoacrylate + NH(3).
(Z)-3-ureidoacrylate + H(2)O = (Z)-3-aminoacrylate + CO(2) + NH(3).
(Z)-2-methyl-ureidoacrylate peracid + H(2)O = (Z)-2-methyl-peroxyaminoacrylate + CO(2) + NH(3).
Protein Details
3. 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).