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Peroxyaminoacrylate (M2MDB001682)

Record Information
Version2.0
Creation Date2012-07-30 14:55:10 -0600
Update Date2015-06-03 17:21:04 -0600
Secondary Accession Numbers
  • ECMDB21275
Identification
Name:Peroxyaminoacrylate
DescriptionPeroxyaminoacrylate is a member of the chemical class known as Enones. These are compounds containing the enone functional group, with the structure RC(=O)CR'.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2Z)-3-aminoprop-2-eneperoxoate
  • (2Z)-3-aminoprop-2-eneperoxoic acid
  • (Z)-3-Peroxyaminoacrylate
  • (Z)-3-Peroxyaminoacrylic acid
  • Aminoacrylate peracid
  • Aminoacrylic acid peracid
  • Peroxy aminoacrylate
  • Peroxy aminoacrylic acid
  • Peroxyaminoacrylate
  • Peroxyaminoacrylic acid
Chemical Formula:C3H5NO3
Weight:Average: 103.0767
Monoisotopic: 103.026943031
InChI Key:WQKGFGLGYOHJOG-UPHRSURJSA-N
InChI:InChI=1S/C3H5NO3/c4-2-1-3(5)7-6/h1-2,6H,4H2/b2-1-
CAS number:Not Available
IUPAC Name:(2Z)-3-aminoprop-2-eneperoxoic acid
Traditional IUPAC Name:peroxyaminoacrylate
SMILES:N\C=C/C(=O)OO
Chemical Taxonomy
Description belongs to the class of organic compounds known as peroxycarboxylic acids. These are organic acids with the general formula [H]OOC(R)=O (R = H, organyl group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassPeroxycarboxylic acids and derivatives
Direct ParentPeroxycarboxylic acids
Alternative Parents
Substituents
  • Acrylic acid or derivatives
  • Peroxycarboxylic acid
  • Vinylogous amide
  • Amino acid or derivatives
  • Carboxylic acid salt
  • Hydroperoxide
  • Enamine
  • Monocarboxylic acid or derivatives
  • Peroxol
  • Allylamine
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Primary aliphatic amine
  • Organic oxygen compound
  • Primary amine
  • Organic salt
  • Carbonyl group
  • 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 Solubility159 g/LALOGPS
logP-0.64ALOGPS
logP-0.54ChemAxon
logS0.19ALOGPS
pKa (Strongest Acidic)7.39ChemAxon
pKa (Strongest Basic)3.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.56 m³·mol⁻¹ChemAxon
Polarizability8.39 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
NADH + Peroxyaminoacrylate > 3-Aminoacrylate + Water + NAD
Water + Ureidoacrylate peracid > Carbamic acid + Hydrogen ion + Peroxyaminoacrylate
Ureidoacrylate peracid + Water <> Peroxyaminoacrylate + Carbamic acid
Peroxyaminoacrylate <> 3-Aminoacrylate
Peroxyaminoacrylate + a reduced electron acceptor > 3-Aminoacrylate + Water + Hydrogen ion + an oxidized electron acceptor
Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Ammonia
Ureidoacrylate peracid + Water + Carbamic acid + (Z)-2-Methyl-ureidoacrylate peracid <> Peroxyaminoacrylate + Carbon dioxide + Ammonia + (Z)-2-Methyl-peroxyaminoacrylate
Uracil + FMNH2 + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion + Peroxyaminoacrylate
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:
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Uracil degradation IIIPW002026 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fki-9100000000-db715a15c2c4b6f132a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-9000000000-37efe41c00992a9fdb1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-710b7105b933dbcc1dcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-7900000000-97e05fdfcf0d580a19c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-9200000000-0ad740a68dd63cb5df10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uyl-9000000000-83e544387003edc8c285View 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:
  • 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 ID59892
HMDB IDNot Available
Pubchem Compound ID46173085
Kegg IDC20249
ChemSpider ID26331745
Wikipedia IDNot Available
BioCyc IDCPD0-2340
EcoCyc IDCPD0-2340

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 monooxygenase rutA
General function:
Involved in oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific function:
Part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:
rutA
Uniprot ID:
P75898
Molecular weight:
42219
Reactions
Uracil + FMNH(2) + O(2) = (Z)-3-ureidoacrylate peracid + FMN + H(2)O.
Thymine + FMNH(2) + O(2) = (Z)-2-methylureidoacrylate peracid + FMN + H(2)O.
Protein Details
3. 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).