11280714432D 1   1.00000     0.00000     0

 17 18  0     0  0            999 V2000
    3.9292    0.1833    0.0000 C   0  0  0  0  0  0           0  0  0
    2.5000    0.1833    0.0000 C   0  0  0  0  0  0           0  0  0
    2.5000   -0.6417    0.0000 C   0  0  0  0  0  0           0  0  0
    3.2125    0.5958    0.0000 C   0  0  0  0  0  0           0  0  0
    3.2125   -1.0542    0.0000 N   0  0  3  0  0  0           0  0  0
    3.9292   -0.6417    0.0000 C   0  0  0  0  0  0           0  0  0
    1.7875   -1.0542    0.0000 N   0  0  0  0  0  0           0  0  0
    4.6500    0.5958    0.0000 C   0  0  0  0  0  0           0  0  0
    1.7875    0.5958    0.0000 C   0  0  0  0  0  0           0  0  0
    3.2125    1.4208    0.0000 O   0  0  0  0  0  0           0  0  0
    4.6542    1.4208    0.0000 O   0  0  0  0  0  0           0  0  0
    1.0667   -0.6417    0.0000 C   0  0  0  0  0  0           0  0  0
    5.3625    0.1833    0.0000 O   0  0  0  0  0  0           0  0  0
    1.0667    0.1833    0.0000 C   0  0  0  0  0  0           0  0  0
    3.2125   -1.8792    0.0000 C   0  0  0  0  0  0           0  0  0
    0.3500   -1.0625    0.0000 C   0  0  0  0  0  0           0  0  0
    3.9250   -2.2917    0.0000 C   0  0  0  0  0  0           0  0  0
  2  4  1  0     0  0
  3  5  1  0     0  0
  4  1  1  0     0  0
  5  6  1  0     0  0
  6  1  2  0     0  0
  7  3  2  0     0  0
  8  1  1  0     0  0
  9  2  2  0     0  0
 10  4  2  0     0  0
 11  8  2  0     0  0
 12  7  1  0     0  0
 13  8  1  0     0  0
 14  9  1  0     0  0
 15  5  1  0     0  0
 16 12  1  0     0  0
 17 15  1  0     0  0
  2  3  1  0     0  0
 14 12  2  0     0  0
M  END
> <ID>
CHEBI:100147

> <NAME>
nalidixic acid

> <DEFINITION>
A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively. An orally administered antibacterial, it is used in the treatment of lower urinary-tract infections due to Gram-negative bacteria, including the majority of E. coli, Enterobacter, Klebsiella, and Proteus species.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:7456

> <SYNONYM>
NALIDIXIC ACID; Nalidixic acid; 3-carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one; 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid; 1-ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid; 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid; 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure; 1,4-dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid

> <IUPAC_NAME>
1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

> <INN>
nalidixic acid; acidum nalidixicum; acido nalidixico; acide nalidixique

> <FORMULA>
C12H12N2O3

> <MASS>
232.23530

> <MONOISOTOPIC_MASS>
232.08479

> <CHARGE>
0

> <SMILES>
CCn1cc(C(O)=O)c(=O)c2ccc(C)nc12

> <INCHI>
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

> <INCHIKEY>
MHWLWQUZZRMNGJ-UHFFFAOYSA-N

> <CAS_REGISTRY_NUMBER>
389-08-2

> <REAXYS_REGISTRY_NUMBER>
750515

> <CHEMIDPLUS>
389-08-2

> <DRUGBANK_ACCESSION>
DB00779

> <KEGG_COMPOUND_ACCESSION>
C05079

> <KEGG_DRUG_ACCESSION>
D00183

> <LINCS_ACCESSION>
LSM-5590

> <PDBECHEM_ACCESSION>
NIX

> <WIKIPEDIA_ACCESSION>
Nalidixic_Acid

> <PUBMED_CITATION>
11321869; 12002106; 12399485; 12702698; 14107587; 16107187; 16423473; 16667857; 16803589; 17132068; 17631104; 18788798; 19071706; 28166217

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