Ureidoacrylate peracid (ECMDB21299) (M2MDB001703)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (75)
Record Information
Version2.0
Creation Date2012-07-30 14:55:16 -0600
Update Date2015-06-03 17:21:06 -0600
Secondary Accession Numbers
  • ECMDB21299
Identification
Name:Ureidoacrylate peracid
DescriptionUreidoacrylate peracid 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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (2Z)-3-(carbamoylamino)prop-2-eneperoxoate
  • (2Z)-3-(carbamoylamino)prop-2-eneperoxoic acid
  • (Z)-3-Ureidoacrylate peracid
  • (Z)-3-Ureidoacrylic acid peracid
  • Peroxy ureidoacrylate
  • Peroxy ureidoacrylic acid
  • Ureidoacrylate peracid
  • Ureidoacrylic acid peracid
  • Ureidoperacrylate
  • Ureidoperacrylic acid
Chemical Formula:C4H6N2O4
Weight:Average: 146.1014
Monoisotopic: 146.03275669
InChI Key:AJFKXWQDHFYKFK-UPHRSURJSA-N
InChI:InChI=1S/C4H6N2O4/c5-4(8)6-2-1-3(7)10-9/h1-2,9H,(H3,5,6,8)/b2-1-
CAS number:Not Available
IUPAC Name:(2Z)-3-(carbamoylamino)prop-2-eneperoxoic acid
Traditional IUPAC Name:ureidoacrylate peracid
SMILES:NC(=O)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
  • Peroxycarboxylic acid
  • Vinylogous amide
  • Acrylic acid or derivatives
  • Carboxylic acid salt
  • Carbonic acid derivative
  • Hydroperoxide
  • Urea
  • Monocarboxylic acid or derivatives
  • Peroxol
  • Organic salt
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • 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 Solubility10.6 g/LALOGPS
logP-1.2ALOGPS
logP-1.1ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)7.39ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.65 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.68 m³·mol⁻¹ChemAxon
Polarizability12.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Hydrogen ion + NADH + Oxygen + Uracil > NAD + Ureidoacrylate peracid
Water + Ureidoacrylate peracid > Carbamic acid + Hydrogen ion + Peroxyaminoacrylate
Uracil + FMNH + Oxygen <> Ureidoacrylate peracid + Flavin Mononucleotide
Ureidoacrylate peracid + Water <> Peroxyaminoacrylate + Carbamic acid
Ureidoacrylate peracid + NADH > 3-ureidoacrylate + NAD + Water
Uracil + Oxygen + FMNH > Hydrogen ion + Ureidoacrylate peracid + Flavin Mononucleotide
Uracil + FMNH(2) + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Water
Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Ammonia
Ureidoacrylate peracid + Water + Carbamic acid + (Z)-2-Methyl-ureidoacrylate peracid <> Peroxyaminoacrylate + Carbon dioxide + Ammonia + (Z)-2-Methyl-peroxyaminoacrylate
Uracil + FMNH + Oxygen + Thymine <> Ureidoacrylate peracid + Flavin Mononucleotide + (Z)-2-Methyl-ureidoacrylate peracid
Uracil + FMNH2 + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion + Peroxyaminoacrylate
Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Carbamic acid + Hydrogen ion + 3-Aminoacrylate
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_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ims-5900000000-e09eb9069f27daac030cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9400000000-28f6cd16f183162675bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9000000000-7440c5541e26730d7232View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udm-6900000000-2e7b95c6ed43e9dbd802View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hgo-9500000000-3ce71556d586d9948f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-466750df6de7c7555069View in MoNA
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 ID59889
HMDB IDNot Available
Pubchem Compound ID46173244
Kegg IDC20231
ChemSpider ID26331742
Wikipedia IDNot Available
BioCyc IDCPD0-2338
EcoCyc IDCPD0-2338

Enzymes

Protein Details
1. Putative flavin reductase rutF
General function:
Involved in FMN binding
Specific function:
Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:
rutF
Uniprot ID:
P75893
Molecular weight:
17749
Reactions
FMNH(2) + NAD(+) = FMN + NADH.
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).