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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL5
CHEMBL5
Compound Name NALIDIXIC ACID
ChEMBL Synonyms Wintomylon | WIN 18,320 | WIN 18,320-3 | NALIDIXANE | NALIDIXATE SODIUM | Uroneg | NALIX | NALIDIXIC ACID | URIBEN | Neg Gram | NEGGRAM | MICTRAL | NEGRAM
Max Phase 4 (Approved)
Trade Names NALIDIXIC ACID | NALIX | Uroneg | Wintomylon | NEGRAM | MICTRAL | NEGGRAM | Neg Gram | URIBEN
Molecular Formula C12H12N2O3

Additional synonyms for CHEMBL5 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCN1C=C(C(=O)O)C(=O)c2ccc(C)nc12
Standard InChI InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13- ...
Download InChI
Standard InChI Key MHWLWQUZZRMNGJ-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL5

Molecule Features

CHEMBL5 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Discontinued

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial DNA gyrase inhibitor Bacterial DNA gyrase FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials

Clinical Data

ClinicalTrials.gov NALIDIXIC ACID
The Cochrane Collaboration NALIDIXIC ACID

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL5. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 0.943
CHEMBL2470 Cannabinoid CB2 receptor Rattus norvegicus 0.835
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.577
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.442
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 0.232

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2470 Cannabinoid CB2 receptor Rattus norvegicus 0.739
CHEMBL3691 Autotaxin Homo sapiens 0.590
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.523
CHEMBL2366505 Integrase Human immunodeficiency virus 1 0.410
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.346
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.335
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.304
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.252
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 0.229
CHEMBL3471 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 0.221

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
232.2 232.0848 1.42 2 72.19 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 0 5 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
3.45 6.12 .03 -1.54 2 17 0.85

Structural Alerts

There are 2 structural alerts for CHEMBL5. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01M - QUINOLONE ANTIBACTERIALS
J01MB - Other quinolones
J01MB02 - nalidixic acid

ChemSpider ChemSpider:MHWLWQUZZRMNGJ-UHFFFAOYSA-N
PubChem SID: 120913 SID: 124883418 SID: 144204386 SID: 144208675 SID: 144213071 SID: 170465215 SID: 17389812 SID: 174006246 SID: 26746931 SID: 26751459 SID: 26751460 SID: 56422386 SID: 855620 SID: 90340622
Wikipedia Nalidixic_acid

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL5



ACToR 389-08-2
BindingDB 21691
Brenda 2148 114048
ChEBI 100147
ChemicalBook CB1194283
DrugBank DB00779
DrugCentral 1875
eMolecules 529362
EPA CompTox Dashboard DTXSID3020912
FDA SRS 3B91HWA56M
Human Metabolome Database HMDB0014917
IBM Patent System DD9C87459816EE51C7B5314639D8FCB5
KEGG Ligand C05079
LINCS LSM-5590
Mcule MCULE-6808033849
MolPort MolPort-001-769-233
NIH Clinical Collection SAM002554914
Nikkaji J2.039G
NMRShiftDB 20123603
PDBe NIX
PharmGKB PA164746384
PubChem 4421
PubChem: Thomson Pharma 14773844
Selleck Nalidixic-acid(NegGram)
SureChEMBL SCHEMBL21736
ZINC ZINC000000057421

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/MHWLWQUZZRMNGJ-UHFFFAOYSA-N spacer
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