Ketcher 04261610582D 1   1.00000     0.00000     0

 17 18  0     0  0            999 V2000
   22.6631  -40.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8541  -40.8685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9030  -40.5594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6951  -39.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7440  -39.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9350  -39.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1260  -39.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4350  -38.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4350  -38.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1749  -39.5813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4318  -38.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9670  -40.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1631  -41.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1631  -41.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4721  -40.8685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6631  -39.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7508  -42.6286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0     0  0
  2  3  1  0     0  0
  3  4  2  0     0  0
  4  5  1  0     0  0
  5  6  1  0     0  0
  6  7  1  0     0  0
  7  8  2  0     0  0
  8  9  1  0     0  0
  5  9  2  0     0  0
  7 10  1  0     0  0
 10 11  1  0     0  0
 10 12  2  0     0  0
  2 13  1  0     0  0
 13 14  1  0     0  0
 14 15  1  0     0  0
  1 15  1  0     0  0
  1 16  2  0     0  0
 14 17  2  0     0  0
M  CHG  2  10   1  11  -1
M  END
> <ID>
CHEBI:71415

> <NAME>
nitrofurantoin

> <DEFINITION>
An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:7591

> <SYNONYM>
N-(5-Nitrofurfurylidene)-1-aminohydantoin; 5-Nitrofurantoin; 1-[(5-Nitrofurfurylidene)amino]hydantoin; 1-(5-Nitro-2-furfurylideneamino)hydantoin; 1-(5-Nitro-2-furfurylidenamino)hydantoin; 1-((5-Nitrofurfurylidene)amino)hydantoin

> <IUPAC_NAME>
1-{[(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione

> <INN>
nitrofurantoinum; nitrofurantoine; nitrofurantoina; nitrofurantoin

> <FORMULA>
C8H6N4O5

> <MASS>
238.157

> <MONOISOTOPIC_MASS>
238.03382

> <CHARGE>
0

> <SMILES>
C1(N(/N=C/C=2OC(=CC2)[N+]([O-])=O)CC(N1)=O)=O

> <INCHI>
InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+

> <INCHIKEY>
NXFQHRVNIOXGAQ-YCRREMRBSA-N

> <CAS_REGISTRY_NUMBER>
67-20-9

> <REAXYS_REGISTRY_NUMBER>
8132135

> <CHEMIDPLUS>
67-20-9

> <DRUGBANK_ACCESSION>
DB00698

> <KEGG_COMPOUND_ACCESSION>
C07268

> <KEGG_DRUG_ACCESSION>
D00439

> <NIST_CHEMISTRY_WEBBOOK>
67-20-9

> <WIKIPEDIA_ACCESSION>
Nitrofurantoin

> <PUBMED_CITATION>
21567157; 22240115; 22252772; 22252808; 22285235; 22332195; 22508296; 22535452; 22552451; 22722224; 22779302; 22787489; 22836745; 22857139; 22869929; 22876623; 22923965; 22929632; 22977056; 23016316; 23109011; 23113731; 23114172

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