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


(Z)-3-Ureidoacrylate (M2MDB003517)

Record Information
Version2.0
Creation Date2012-10-10 12:17:43 -0600
Update Date2015-06-03 17:25:59 -0600
Secondary Accession Numbers
  • ECMDB23127
Identification
Name:(Z)-3-Ureidoacrylate
Description(Z)-3-Ureidoacrylate is an intermediate in the degradation of pyrimidines. It is a substrate for the enzyme Peroxyureidoacrylate/ureidoacrylate amidohydrolase which catalyzes the reaction (Z)-3-ureidoacrylate peracid + H(2)O = (Z)-3-peroxyaminoacrylate + NH(3). This enzyme quickly hydrolyzes the ureidoacrylate peracid to avoid toxicity, but can also hydrolyzes ureidoacrylate that is formed spontaneously from ureidoacrylate peracid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2Z)-3-(carbamoylamino)Acrylate
  • (2Z)-3-(Carbamoylamino)acrylic acid
  • (Z)-3-(carbamoylamino)Prop-2-enoate
  • (Z)-3-(carbamoylamino)prop-2-enoic acid
  • (Z)-3-ureido-2-Propenoate
  • (Z)-3-ureido-2-propenoic acid
  • (Z)-3-Ureidoacrylic acid
  • Ureidoacrylate
  • Ureidoacrylic acid
Chemical Formula:C4H6N2O3
Weight:Average: 130.102
Monoisotopic: 130.037842068
InChI Key:JDSSVQWHYUVDDF-UPHRSURJSA-N
InChI:InChI=1S/C4H6N2O3/c5-4(9)6-2-1-3(7)8/h1-2H,(H,7,8)(H3,5,6,9)/b2-1-
CAS number:Not Available
IUPAC Name:(2Z)-3-[(C-hydroxycarbonimidoyl)amino]prop-2-enoic acid
Traditional IUPAC Name:(2Z)-3-(C-hydroxycarbonimidoylamino)prop-2-enoic acid
SMILES:[H]\C(NC(O)=N)=C(/[H])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
  • Urea
  • Carbonic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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 Solubility2.2 g/LALOGPS
logP-0.9ALOGPS
logP-1.9ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.98 m³·mol⁻¹ChemAxon
Polarizability11.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(Z)-3-Ureidoacrylate + Water > 3-Aminoacrylate + Carbon dioxide + Ammonia
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-9800000000-be7f065daa29e9f9a4cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-1a68f2e87e634d44d2b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-e0115b9a01fd552fda1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002u-9300000000-6a8d059f4ed54a895f5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9100000000-6bc4311acdd6ef9883d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4356dbb2d89d67dc4377View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID59890
HMDB IDNot Available
Pubchem Compound ID1751484
Kegg IDC20254
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 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).