Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


Ureidoacrylate peracid (M2MDB001703)

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).