ChemFOnt: Showing chemical card for Nalidixic Acid (CFc000009244)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:19 UTC

Chemfont ID

CFc000009244

Molecule Identification

Common Name

Nalidixic Acid

Definition

Nalidixic Acid is only found in individuals that have used or taken this drug. It is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase. [PubChem]Evidence exists for Nalidixic acid that its active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid	ChEBI
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure	ChEBI
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid	ChEBI
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid	ChEBI
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid	ChEBI
3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one	ChEBI
Acide nalidixique	ChEBI
Acido nalidixico	ChEBI
Acidum nalidixicum	ChEBI
NA	Kegg
NegGram	Kegg
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate	Generator
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate	Generator
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylate	Generator
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate	Generator
Nalidixate	Generator
Acid, nalidixic	HMDB
Nevigramon	HMDB
Sodium, nalidixate	HMDB
Nalidixate sodium	HMDB
Nalidixin	HMDB
Sodium nalidixic acid, anhydrous	HMDB
Anhydrous, nalidixate sodium	HMDB
Nalidixate sodium anhydrous	HMDB
Sodium anhydrous, nalidixate	HMDB
Sodium nalidixic acid, monohydrate	HMDB

Chemical Formula

C₁₂H₁₂N₂O₃

Average Molecular Weight

232.2353

Monoisotopic Molecular Weight

232.08479226

IUPAC Name

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

Traditional Name

nalidixic acid

CAS Registry Number

389-08-2

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2

InChI Identifier

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)

InChI Key

MHWLWQUZZRMNGJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridine carboxylic acids and derivatives

Alternative Parents

Substituents

Naphthyridine carboxylic acid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Methylpyridine
Pyridine
Heteroaromatic compound
Vinylogous amide
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:100147 )
1,8-naphthyridine derivative (CHEBI:100147 )
quinolone antibiotic (CHEBI:100147 )
4-Quinolones (C05079 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014917)

Source

Exogenous

Exogenous (HMDB: HMDB0014917)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Anti-infective (HMDB: HMDB0014917)

Enzyme Inhibitor (HMDB: HMDB0014917)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.3 g/L	ALOGPS
logP	0.95	ALOGPS
logP	1.01	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	5.95	ChemAxon
pKa (Strongest Basic)	4.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.5 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.82 m³·mol⁻¹	ChemAxon
Polarizability	23.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon