Showing metabocard for (Z)-3-Ureidoacrylate (MMDBc0031767)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:48:30 UTC
Update Date2022-08-31 18:24:29 UTC
Metabolite IDMMDBc0031767
Metabolite Identification
Common 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
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x000055c79c43cbc8>


  Mrv0541 10101211172D          

 11 10  0  0  0  0            999 V2000
    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
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.0000    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
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  1  1  0  0  0  0
 11  2  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x000055c79c43cbc8>

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3D SDF for #<Metabolite:0x000055c79c43cbc8>

  Mrv0541 10101211172D          

 11 10  0  0  0  0            999 V2000
    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
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.0000    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
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  1  1  0  0  0  0
 11  2  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031767

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H6N2O3/c5-4(9)6-2-1-3(7)8/h1-2H,(H,7,8)(H3,5,6,9)/b2-1-

> <INCHI_KEY>
JDSSVQWHYUVDDF-UPHRSURJSA-N

> <FORMULA>
C4H6N2O3

> <MOLECULAR_WEIGHT>
130.102

> <EXACT_MASS>
130.037842068

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
11.123461123842745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-3-[(C-hydroxycarbonimidoyl)amino]prop-2-enoic acid

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-1.9274165565196204

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.934059791869142

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0520234566701436

> <JCHEM_PKA_STRONGEST_BASIC>
9.41934044339726

> <JCHEM_POLAR_SURFACE_AREA>
93.41000000000001

> <JCHEM_REFRACTIVITY>
39.9837

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(C-hydroxycarbonimidoylamino)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x000055c79c43cbc8>
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PDB for #<Metabolite:0x000055c79c43cbc8>
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  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3   10                                                  
CONECT    2    1    6   11                                                  
CONECT    3    1    7    8                                                  
CONECT    4    5    6    9                                                  
CONECT    5    4                                                            
CONECT    6    2    4                                                       
CONECT    7    3                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    1                                                            
CONECT   11    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x000055c79c43cbc8>
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SMILES for #<Metabolite:0x000055c79c43cbc8>
[H]\C(NC(O)=N)=C(/[H])C(O)=O
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INCHI for #<Metabolite:0x000055c79c43cbc8>
InChI=1S/C4H6N2O3/c5-4(9)6-2-1-3(7)8/h1-2H,(H,7,8)(H3,5,6,9)/b2-1-
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Synonyms
ValueSource
(Z)-3-Ureido-2-propenoic acidChEBI
(Z)-3-Ureido-2-propenoateGenerator
(Z)-3-Ureidoacrylic acidGenerator
(Z)-3-UreidoacrylateKEGG
Ureidoacrylic acidGenerator
Molecular FormulaC4H6N2O3
Average Mass130.102
Monoisotopic Mass130.037842068
IUPAC Name(2Z)-3-[(C-hydroxycarbonimidoyl)amino]prop-2-enoic acid
Traditional Name(2Z)-3-(C-hydroxycarbonimidoylamino)prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(NC(O)=N)=C(/[H])C(O)=O
InChI Identifier
InChI=1S/C4H6N2O3/c5-4(9)6-2-1-3(7)8/h1-2H,(H,7,8)(H3,5,6,9)/b2-1-
InChI KeyJDSSVQWHYUVDDF-UPHRSURJSA-N