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(Z)-2-Methyl-peroxyaminoacrylate (M2MDB003515)

Record Information
Version2.0
Creation Date2012-10-10 12:17:39 -0600
Update Date2015-06-03 17:25:58 -0600
Secondary Accession Numbers
  • ECMDB23125
Identification
Name:(Z)-2-Methyl-peroxyaminoacrylate
Description(Z)-2-Methyl-peroxyaminoacrylate is an intermediate in the degradation of exogenous pyrimidines via the RutB pathway. 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-amino-2-Methyl-2-propeneperoxoate
  • (2Z)-3-Amino-2-methyl-2-propeneperoxoic acid
  • (Z)-2-hydroxy-3-peroxyaminoacrylate
  • (Z)-2-Hydroxy-3-peroxyaminoacrylic acid
  • (Z)-2-Methyl-peroxyaminoacrylic acid
  • (Z)-2-Methylperoxyaminoacrylate
  • (Z)-2-Methylperoxyaminoacrylic acid
  • (Z)-3-amino-2-Methylprop-2-eneperoxoate
  • (Z)-3-amino-2-methylprop-2-eneperoxoic acid
Chemical Formula:C4H7NO3
Weight:Average: 117.1033
Monoisotopic: 117.042593095
InChI Key:DYYSAMFOJRGAMQ-IHWYPQMZSA-N
InChI:InChI=1S/C4H7NO3/c1-3(2-5)4(6)8-7/h2,7H,5H2,1H3/b3-2-
CAS number:Not Available
IUPAC Name:(2Z)-3-amino-2-methylprop-2-eneperoxoic acid
Traditional IUPAC Name:(2Z)-3-amino-2-methylprop-2-eneperoxoic acid
SMILES:[H]\C(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
  • 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 Solubility103 g/LALOGPS
logP-0.35ALOGPS
logP-0.15ChemAxon
logS-0.05ALOGPS
pKa (Strongest Acidic)7.36ChemAxon
pKa (Strongest Basic)3.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.92 m³·mol⁻¹ChemAxon
Polarizability10.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(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
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_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-067i-9800000000-85c460292b4daaabdd31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o0-9200000000-b5da1624185ddca33d03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-d7bcd160e640a4faf27aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-aa48dc8acc25f5651923View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-9500000000-c1cce8096eb976a6f11bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uyi-9000000000-96cc642ea5aae042e2d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9100000000-ff794d5b0dee2ae71c18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-e72e92c1dbcd2e48e59dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-2b671d7ac52b830cbafdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-42f0a2ebd8b75ef48eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-9100000000-04957a91bf9579c747c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-9000000000-ee4f7adb0930dde995d1View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID63250
HMDB IDHMDB0304002
Pubchem Compound ID56927732
Kegg IDC20250
ChemSpider ID26333052
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).