Showing metabocard for nitrofurazone (MMDBc0032862)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 22:03:18 UTC
Update Date2022-08-31 21:44:38 UTC
Metabolite IDMMDBc0032862
Metabolite Identification
Common Namenitrofurazone
DescriptionA semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wo
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be1fa89d8>


  Mrv1652309112120092D          

 14 14  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9405   -1.9851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7911   -0.5640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  2  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  CHG  2   6   1   8  -1
M  END
Download

3D MOL for #<Metabolite:0x0000560be1fa89d8>

HMDB0257247
     RDKit          3D
Rivafurazon
 20 20  0  0  0  0  0  0  0  0999 V2000
    4.8337    0.6645    0.6950 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4765    0.2699    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0472    0.0138    2.0655 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145    0.1655   -0.2356 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -0.2180   -0.0424 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2877    0.5375   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611    0.0451    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779   -1.2679    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7485   -1.3375    0.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2078   -0.0787    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    0.2782    0.2405 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.4873   -0.5522    0.5210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    1.5680   -0.0756 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2004    0.6777   -0.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167    1.5745    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4398   -0.0288    0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0059    0.3831   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089    1.5692   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6643   -2.0523    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3389   -2.2118    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14  7  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
M  CHG  2  11   1  13  -1
M  END
Download

3D SDF for #<Metabolite:0x0000560be1fa89d8>


  Mrv1652309112120092D          

 14 14  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9405   -1.9851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7911   -0.5640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  2  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  CHG  2   6   1   8  -1
M  END
> <DATABASE_ID>
MMDBc0032862

> <DATABASE_NAME>
MIME

> <SMILES>
NC(=O)NN=CC1=CC=C(O1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)

> <INCHI_KEY>
IAIWVQXQOWNYOU-UHFFFAOYSA-N

> <FORMULA>
C6H6N4O4

> <MOLECULAR_WEIGHT>
198.138

> <EXACT_MASS>
198.038904689

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
17.100779620871243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(5-nitrofuran-2-yl)methylidene]amino}urea

> <ALOGPS_LOGP>
0.23

> <JCHEM_LOGP>
-0.13506338633333326

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.213885115106688

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.794831274785802

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9815602115668405

> <JCHEM_POLAR_SURFACE_AREA>
123.76

> <JCHEM_REFRACTIVITY>
44.2064

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-nitrofurfural semicarbazone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000560be1fa89d8>

HMDB0257247
     RDKit          3D
Rivafurazon
 20 20  0  0  0  0  0  0  0  0999 V2000
    4.8337    0.6645    0.6950 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4765    0.2699    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0472    0.0138    2.0655 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145    0.1655   -0.2356 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -0.2180   -0.0424 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2877    0.5375   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611    0.0451    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779   -1.2679    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7485   -1.3375    0.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2078   -0.0787    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    0.2782    0.2405 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.4873   -0.5522    0.5210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    1.5680   -0.0756 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2004    0.6777   -0.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167    1.5745    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4398   -0.0288    0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0059    0.3831   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089    1.5692   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6643   -2.0523    0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3389   -2.2118    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14  7  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
M  CHG  2  11   1  13  -1
M  END
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PDB for #<Metabolite:0x0000560be1fa89d8>

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.060   3.620   0.000  0.00  0.00           N+1
HETATM    7  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O-1
HETATM    9  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -2.147  -1.375   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      -3.052  -2.621   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.584  -2.460   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.489  -3.706   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      -5.210  -1.053   0.000  0.00  0.00           N+0
CONECT    1    2    5                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for #<Metabolite:0x0000560be1fa89d8>

COMPND    HMDB0257247
HETATM    1  N1  UNL     1       4.834   0.665   0.695  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.476   0.270   0.887  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.047   0.014   2.066  1.00  0.00           O  
HETATM    4  N2  UNL     1       2.615   0.166  -0.236  1.00  0.00           N  
HETATM    5  N3  UNL     1       1.298  -0.218  -0.042  1.00  0.00           N  
HETATM    6  C2  UNL     1       0.288   0.538  -0.171  1.00  0.00           C  
HETATM    7  C3  UNL     1      -1.061   0.045   0.054  1.00  0.00           C  
HETATM    8  C4  UNL     1      -1.378  -1.268   0.421  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.749  -1.337   0.536  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.208  -0.079   0.237  1.00  0.00           C  
HETATM   11  N4  UNL     1      -4.604   0.278   0.240  1.00  0.00           N1+
HETATM   12  O2  UNL     1      -5.487  -0.552   0.521  1.00  0.00           O  
HETATM   13  O3  UNL     1      -4.939   1.568  -0.076  1.00  0.00           O1-
HETATM   14  O4  UNL     1      -2.200   0.678  -0.033  1.00  0.00           O  
HETATM   15  H1  UNL     1       5.217   1.575   1.041  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.440  -0.029   0.173  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.006   0.383  -1.175  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.409   1.569  -0.451  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.664  -2.052   0.578  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.339  -2.212   0.807  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3    3    4
CONECT    4    5   17
CONECT    5    6    6
CONECT    6    7   18
CONECT    7    8    8   14
CONECT    8    9   19
CONECT    9   10   10   20
CONECT   10   11   14
CONECT   11   12   12   13
END
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SMILES for #<Metabolite:0x0000560be1fa89d8>

NC(=O)NN=CC1=CC=C(O1)[N+]([O-])=O
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INCHI for #<Metabolite:0x0000560be1fa89d8>

InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)
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Synonyms
ValueSource
(5-Nitro-2-furfurylidenamino)ureaChEBI
1-(5-Nitro-2-furfurylidene)semicarbazideChEBI
5-Nitro-2-furaldehyde semicarbazoneChEBI
5-Nitrofuraldehyde semicarbazideChEBI
5-Nitrofuran-2-carbaldehyde semicarbazoneChEBI
5-Nitrofurfural semicarbazoneChEBI
AlfucinChEBI
AmifurChEBI
ChemofuranChEBI
FuracillinChEBI
FuracinChEBI
FuracinettenChEBI
FuracoccidChEBI
FuraldonChEBI
Furazol WChEBI
FuresolChEBI
MammexChEBI
MastofuranChEBI
MonafuracinChEBI
NifuzonChEBI
NitrofuralChEBI
NitrofuralumChEBI
Molecular FormulaC6H6N4O4
Average Mass198.138
Monoisotopic Mass198.038904689
IUPAC Name{[(5-nitrofuran-2-yl)methylidene]amino}urea
Traditional Name5-nitrofurfural semicarbazone
CAS Registry NumberNot Available
SMILES
NC(=O)NN=CC1=CC=C(O1)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)
InChI KeyIAIWVQXQOWNYOU-UHFFFAOYSA-N