Showing metabocard for (Z)-2-Methyl-peroxyaminoacrylate (MMDBc0031766)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:48:27 UTC
Update Date2022-08-31 18:24:29 UTC
Metabolite IDMMDBc0031766
Metabolite Identification
Common 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb2432e518>


  Mrv0541 10101211172D          

  9  8  0  0  0  0            999 V2000
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb2432e518>

HMDB0304002
     RDKit          3D
(Z)-2-methyl-peroxyaminoacrylate
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.4211   -1.8672   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3759   -0.3832   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790    0.3166   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4741    1.7382   -0.4625 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8775    0.2941   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    1.5446    0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0348   -0.4380    0.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2143    0.0909    0.4599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697   -2.3304    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2936   -2.1982   -0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -2.2043   -0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4218   -0.1827   -0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6629    2.3445   -1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    2.1973    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013    1.0778    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  8 15  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb2432e518>


  Mrv0541 10101211172D          

  9  8  0  0  0  0            999 V2000
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031766

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(N)=C(/C)C(=O)OO

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO3/c1-3(2-5)4(6)8-7/h2,7H,5H2,1H3/b3-2-

> <INCHI_KEY>
DYYSAMFOJRGAMQ-IHWYPQMZSA-N

> <FORMULA>
C4H7NO3

> <MOLECULAR_WEIGHT>
117.1033

> <EXACT_MASS>
117.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
10.598872528972912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-3-amino-2-methylprop-2-eneperoxoic acid

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
-0.1467260036666666

> <ALOGPS_LOGS>
-0.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.359317465366349

> <JCHEM_PKA_STRONGEST_BASIC>
3.7096961901667274

> <JCHEM_POLAR_SURFACE_AREA>
72.55000000000001

> <JCHEM_REFRACTIVITY>
26.920700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-amino-2-methylprop-2-eneperoxoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb2432e518>

HMDB0304002
     RDKit          3D
(Z)-2-methyl-peroxyaminoacrylate
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.4211   -1.8672   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3759   -0.3832   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790    0.3166   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4741    1.7382   -0.4625 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8775    0.2941   -0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    1.5446    0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0348   -0.4380    0.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2143    0.0909    0.4599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697   -2.3304    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2936   -2.1982   -0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -2.2043   -0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4218   -0.1827   -0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6629    2.3445   -1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    2.1973    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013    1.0778    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  8 15  1  0
M  END
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PDB for #<Metabolite:0x00007fdb2432e518>

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    3    5    9                                                  
CONECT    3    1    2    4                                                  
CONECT    4    3    6    8                                                  
CONECT    5    2                                                            
CONECT    6    4                                                            
CONECT    7    8                                                            
CONECT    8    4    7                                                       
CONECT    9    2                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00007fdb2432e518>

COMPND    HMDB0304002
HETATM    1  C1  UNL     1      -0.421  -1.867  -0.377  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.376  -0.383  -0.312  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.479   0.317  -0.517  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.474   1.738  -0.462  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.878   0.294  -0.023  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.938   1.545   0.037  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.035  -0.438   0.192  1.00  0.00           O  
HETATM    8  O3  UNL     1       3.214   0.091   0.460  1.00  0.00           O  
HETATM    9  H1  UNL     1      -0.370  -2.330   0.629  1.00  0.00           H  
HETATM   10  H2  UNL     1      -1.294  -2.198  -0.964  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.504  -2.204  -0.919  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.422  -0.183  -0.734  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.663   2.345  -1.290  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.271   2.197   0.452  1.00  0.00           H  
HETATM   15  H7  UNL     1       3.201   1.078   0.257  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    5
CONECT    3    4   12
CONECT    4   13   14
CONECT    5    6    6    7
CONECT    7    8
CONECT    8   15
END
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SMILES for #<Metabolite:0x00007fdb2432e518>

[H]\C(N)=C(/C)C(=O)OO
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INCHI for #<Metabolite:0x00007fdb2432e518>

InChI=1S/C4H7NO3/c1-3(2-5)4(6)8-7/h2,7H,5H2,1H3/b3-2-
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Synonyms
ValueSource
(Z)-2-Methyl-3-peroxyaminoacrylateChEBI
(Z)-2-Methyl-3-peroxyaminoacrylic acidGenerator
(Z)-2-Methyl-3-aminoperacrylateGenerator
(Z)-2-Hydroxy-3-peroxyaminoacrylateChEBI
(Z)-2-Hydroxy-3-peroxyaminoacrylic acidGenerator
(Z)-2-Methyl-peroxyaminoacrylic acidGenerator
(Z)-2-Methylperoxyaminoacrylic acidGenerator
Molecular FormulaC4H7NO3
Average Mass117.1033
Monoisotopic Mass117.042593095
IUPAC Name(2Z)-3-amino-2-methylprop-2-eneperoxoic acid
Traditional Name(2Z)-3-amino-2-methylprop-2-eneperoxoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(N)=C(/C)C(=O)OO
InChI Identifier
InChI=1S/C4H7NO3/c1-3(2-5)4(6)8-7/h2,7H,5H2,1H3/b3-2-
InChI KeyDYYSAMFOJRGAMQ-IHWYPQMZSA-N