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(Z)-2-Methyl-ureidoacrylate peracid (M2MDB003495)

Record Information
Version2.0
Creation Date2012-10-10 12:16:53 -0600
Update Date2015-06-03 17:25:56 -0600
Secondary Accession Numbers
  • ECMDB23105
Identification
Name:(Z)-2-Methyl-ureidoacrylate peracid
Description(Z)-2-Methyl-ureidoacrylate peracid is a substrate of a Putative aminoacrylate peracid reductase which appears to reduce aminoacrylate peracid to aminoacrylate. Cells lacking this protein fail to grow on uridine as the sole source of nitrogen at room temperature indicating a probably accumulation of a toxic intermediate, the peracid aminoacrylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2Z)-3-(carbamoylamino)-2-Methyl-2-propeneperoxoate
  • (2Z)-3-(Carbamoylamino)-2-methyl-2-propeneperoxoic acid
  • (Z)-2-methyl-ureidoacrylate peracid
  • (Z)-2-Methyl-ureidoacrylic acid peracid
  • (Z)-2-Methyl-ureidoperacrylate
  • (Z)-2-methyl-ureidoperacrylic acid
  • (Z)-2-Methylureidoacrylate peracid
  • (Z)-2-Methylureidoacrylic acid peracid
  • (Z)-3-(carbamoylamino)-2-Methylprop-2-eneperoxoate
  • (Z)-3-(carbamoylamino)-2-methylprop-2-eneperoxoic acid
Chemical Formula:C5H8N2O4
Weight:Average: 160.128
Monoisotopic: 160.048406754
InChI Key:GHIKATUDZMBUJC-IHWYPQMZSA-N
InChI:InChI=1S/C5H8N2O4/c1-3(4(8)11-10)2-7-5(6)9/h2,10H,1H3,(H3,6,7,9)/b3-2-
CAS number:Not Available
IUPAC Name:(2Z)-3-[(C-hydroxycarbonimidoyl)amino]-2-methylprop-2-eneperoxoic acid
Traditional IUPAC Name:(2Z)-3-(C-hydroxycarbonimidoylamino)-2-methylprop-2-eneperoxoic acid
SMILES:[H]\C(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
  • 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:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.08 g/LALOGPS
logP-0.51ALOGPS
logP-0.26ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.58ChemAxon
pKa (Strongest Basic)6.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area102.64 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.98 m³·mol⁻¹ChemAxon
Polarizability14.21 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Thymine + FMNH(2) + Oxygen > (Z)-2-Methyl-ureidoacrylate peracid + Flavin Mononucleotide + Water
(Z)-2-Methyl-ureidoacrylate peracid + Water > (Z)-2-Methyl-peroxyaminoacrylate + Carbon dioxide + 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
SMPDB Pathways:
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
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, Positivesplash10-02ta-4900000000-88cc136af0d9cf8fed06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ge9-8900000000-f0263f14019f98c4e638View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a76c177213d3334dc895View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066u-4900000000-4ac9398dd913063cd59bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014m-9600000000-444e0b0b45dec38f479dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-91f99e0c6b15da47b7deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01u3-7900000000-745e23a79497921baba1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0596-9100000000-258dee5fd55117d5d208View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9000000000-8b94ac9f236742230936View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9500000000-6258fd6ad65111a11c47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-f9e84da72d0ee286dbb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c0a51904932f93b8dae6View 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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID63249
HMDB IDHMDB0304003
Pubchem Compound ID56927741
Kegg IDC20232
ChemSpider ID26333051
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 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
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).