Nalidixic acid - Moligand™,≥98% , CAS No.389-08-2

CAS: 389-08-2 Cat. No.: N104920 Molecular Weight: 232.24 Beilstein Registry Number: 750515 EC Number: 206-864-7

GRADE & PURITY Moligand™, ≥98%

Synonyms

Wintomylon | 3-Carboxy-1-ethyl-7-methyl-1,8-naphthidin-4-one | Acide nalidixico [Italian] | Acido nalidissico | Innoxalomn | NALIDIXIC ACID [MART.] | Naldixic acid | Sicmylon | nalidixic acid | Nalidixinsaure | Specifen | 1-Aethyl-7-methyl-1,8-naphthyridi

Storage

Protected from light,Room temperature,Argon charged

Shipped In

Normal

Specifications

Synonyms

Wintomylon | 3-Carboxy-1-ethyl-7-methyl-1, 8-naphthidin-4-one | Acide nalidixico [Italian] | Acido nalidissico | Innoxalomn | NALIDIXIC ACID [MART.] | Naldixic acid | Sicmylon | nalidixic acid | Nalidixinsaure | Specifen | 1-Aethyl-7-methyl-1, 8-naphthyridi

Specifications & Purity

Moligand™, ≥98%

Storage

Protected from light, Room temperature, Argon charged

Shipped In

Normal

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Product Properties

• ALogP: 1.4

Names and Identifiers

• Pubchem Sid: 488179834
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179834
• Canonical Smiles: CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
• IUPAC Name: 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
• InChIKey: MHWLWQUZZRMNGJ-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
• WGK Germany: 2
• RTECS: QN2885000
• UN Number: 3249
• Packing Group: II
• Molecular Weight: 232.24
• Beilstein: 750515
• Reaxy-Rn: 750515
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=750515&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazanaphthalenes
      • Subclass Naphthyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazanaphthalenes
• Subclass: Naphthyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthyridine carboxylic acids and derivatives
• Alternative Parents: Pyridinecarboxylic acids Methylpyridines Vinylogous amides Heteroaromatic compounds Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. These are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
• External Descriptors: 4-Quinolones

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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CXCL8 Tchem Interleukin-8 (642 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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TOP2B Tclin DNA topoisomerase II beta (959 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Homo sapiens (32628 Activities)

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5637 (630 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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Associated Targets(non-human)

Ttr Transthyretin (14 Activities)

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Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Salmonella paratyphi (588 Activities)

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Vibrio anguillarum (183 Activities)

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Streptococcus pneumoniae (31063 Activities)

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Enterococcus (1748 Activities)

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Plasmodium yoelii yoelii (73 Activities)

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Campylobacter jejuni (634 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Pseudomonas putida (467 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella (302 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Proteus vulgaris (5823 Activities)

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Providencia rettgeri (925 Activities)

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Salmonella enterica subsp. enterica serovar Gallinarum (105 Activities)

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Salmonella typhimurium (15756 Activities)

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Shigella boydii (323 Activities)

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Shigella flexneri (1836 Activities)

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Yersinia enterocolitica (166 Activities)

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Aeromonas sobria (43 Activities)

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Vibrio cholerae (1211 Activities)

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Vibrio parahaemolyticus (473 Activities)

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Vibrio vulnificus (80 Activities)

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Plesiomonas shigelloides (58 Activities)

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Pasteurella multocida (1166 Activities)

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Bacteroides fragilis (1445 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Acinetobacter baumannii (41033 Activities)

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Acinetobacter calcoaceticus (618 Activities)

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Neisseria meningitidis (411 Activities)

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Bordetella pertussis (117 Activities)

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Citrobacter freundii (1864 Activities)

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Klebsiella aerogenes (4963 Activities)

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Escherichia coli (133304 Activities)

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Klebsiella oxytoca (929 Activities)

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Morganella morganii (1291 Activities)

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Proteus mirabilis (3894 Activities)

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Salmonella enteritidis (727 Activities)

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Salmonella typhi (4293 Activities)

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Serratia marcescens (3237 Activities)

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Shigella dysenteriae (933 Activities)

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Shigella sonnei (625 Activities)

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Aeromonas hydrophila (292 Activities)

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Vibrio alginolyticus (165 Activities)

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Vibrio fluvialis (60 Activities)

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Haemophilus influenzae (8812 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in diethyl ether, acetone, methylene chloride, chloroform and methanol. Insoluble in water.
• Sensitivity: Air sensitive； Light sensitive
• Melt Point(°C): 229-230°C
• Molecular Weight: 232.230 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 232.085 Da
• Monoisotopic Mass: 232.085 Da
• Topological Polar Surface Area: 70.500 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 378.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xiaoyi Pu, Xin Wang, Youping Liu, Xin Di.  (2023)  A novel deep eutectic solvent-based ultrasound-assisted dispersive liquid–liquid microextraction coupled with high-performance liquid chromatography for the determination of quinolones in environmental water samples.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2023.109374]

2. Yuliya E. Tyutereva, Olga A. Snytnikova, Roman G. Fedunov, Vadim V. Yanshole, Victor F. Plyusnin, Jing Xu, Ivan P. Pozdnyakov.  (2023)  Direct UV photodegradation of nalidixic acid in aqueous solutions: A mechanistic study.  CHEMOSPHERE,      [PMID:37201608] [10.1016/j.chemosphere.2023.138952]

3. Okon Johnson Esua, Da-Wen Sun, Clement Kehinde Ajani, Jun-Hu Cheng, Kevin M. Keener.  (2022)  Modelling of inactivation kinetics of Escherichia coli and Listeria monocytogenes on grass carp treated by combining ultrasound with plasma functionalized buffer.  ULTRASONICS SONOCHEMISTRY,      [PMID:35830785] [10.1016/j.ultsonch.2022.106086]

4. Shang Wu, Yang Yang, Tingwei Wang, Jiadi Sun, Yinzhi Zhang, Jian Ji, Xiulan Sun.  (2021)  Effects of acid, alkaline, cold, and heat environmental stresses on the antibiotic resistance of the Salmonella enterica serovar Typhimurium.  FOOD RESEARCH INTERNATIONAL,      [PMID:34053552] [10.1016/j.foodres.2021.110359]

5. Shiqing Zhou, Ling Li, Yangtao Wu, Shumin Zhu, Ningyuan Zhu, Lingjun Bu, Dionysios D. Dionysiou.  (2020)  UV365 induced elimination of contaminants of emerging concern in the presence of residual nitrite: Roles of reactive nitrogen species.  WATER RESEARCH,      [PMID:32375111] [10.1016/j.watres.2020.115829]

6. Kang Yajing, Wang Yingying, Hou Bingbing, Wang Ruida, Ye Jiang, Zhu Xiaoyu, Wu Haizhen, Zhang Huizhan.  (2019)  AdpAlin, a Pleiotropic Transcriptional Regulator, Is Involved in the Cascade Regulation of Lincomycin Biosynthesis in Streptomyces lincolnensis.  Frontiers in Microbiology,      [PMID:31708899] [10.3389/fmicb.2019.02428]

7. Sandip Mondal, Jianqiao Xu, Guosheng Chen, Siming Huang, Chuyu Huang, Li Yin, Gangfeng Ouyang.  (2018)  Solid-phase microextraction of antibiotics from fish muscle by using MIL-101(Cr)NH2-polyacrylonitrile fiber and their identification by liquid chromatography-tandem mass spectrometry.  ANALYTICA CHIMICA ACTA,      [PMID:30567665] [10.1016/j.aca.2018.09.060]

8. Su Han Wang, Min Lin, Jing Liu, Jian Ping Wang, Ning Peng Wu.  (2025)  Discriminative determination of 15 fluoroquinolones in chicken muscle by Fe3O4@QepA based semi-homogeneous fluorescent array.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.113051]