Oxolinic acid - analytical standard , CAS No.14698-29-4

CAS: 14698-29-4 Cat. No.: O114347 Peso molecular: 261.23 Número EC: 238-750-8

GRADE & PURITY Analytical standard

Synonyms

SPBio_000866 | Uritrate | Oprea1_169598 | HMS2095H07 | KBio2_004445 | KBio3_002579 | NSC110364 | NSC-110364 | Utibid | 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid | Inoxyl | OXOLINIC ACID [MART.] | Acidum oxolinicum | SCHEMBL24

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

A quinoline antibacterial compound and inhibitor of Topo II.

Specifications

Sinónimos

SPBio_000866 | Uritrate | Oprea1_169598 | HMS2095H07 | KBio2_004445 | KBio3_002579 | NSC110364 | NSC-110364 | Utibid | 1-Ethyl-1, 4-dihydro-6, 7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid | Inoxyl | OXOLINIC ACID [MART.] | Acidum oxolinicum | SCHEMBL24

Especificaciones y pureza

analytical standard

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Analytical standard

Nombres e identificadores

• Sonrisas canónicas: CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O
• IUPAC Name: 5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• InChIKey: KYGZCKSPAKDVKC-UHFFFAOYSA-N
• INCHI: 1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
• Isómeros SMILES: CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O
• Peso molecular: 261.23
• Reaxy-Rn: 620635
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=620635&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Quinolines and derivatives
      • Subclass Quinoline carboxylic acids

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Quinolines and derivatives
• Subclass: Quinoline carboxylic acids
• Intermediate Tree Nodes: Not available
• Direct Parent: Quinoline carboxylic acids
• Alternative Parents: Hydroquinolones Hydroquinolines Pyridinecarboxylic acids Benzodioxoles Benzenoids Vinylogous amides Heteroaromatic compounds Acetals Azacyclic compounds Oxacyclic compounds Carboxylic acids Monocarboxylic acids and derivatives Organonitrogen compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Quinoline-3-carboxylic acid - Dihydroquinolone - Dihydroquinoline - Benzodioxole - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Pyridine - Benzenoid - Vinylogous amide - Heteroaromatic compound - Acetal - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Azacycle - Oxacycle - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
• External Descriptors: Quinone fungicides

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

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F2 Tclin Thrombin (11687 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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GABRA1 Tclin GABA receptor alpha-1 subunit (399 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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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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RYR3 Tclin Ryanodine receptor 3 (8 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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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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ARSA Tbio Cerebroside-sulfatase (655 Activities)

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

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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TOP2B Tclin DNA topoisomerase II beta (959 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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HEK293 (82097 Activities)

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

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Ryr2 Ryanodine receptor 2 (21 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Vibrio anguillarum (183 Activities)

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Streptococcus pneumoniae (31063 Activities)

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Plasmodium yoelii yoelii (73 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Enterobacter cloacae (7976 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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Staphylococcus aureus (210822 Activities)

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Acinetobacter sp. (243 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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Proteus mirabilis (3894 Activities)

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Salmonella typhi (4293 Activities)

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Serratia marcescens (3237 Activities)

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Shigella sonnei (625 Activities)

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Streptococcus pyogenes (16140 Activities)

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Enterococcus faecalis (29875 Activities)

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Mycolicibacterium smegmatis (8003 Activities)

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Plasmodium falciparum (966862 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Bursaphelenchus xylophilus (372 Activities)

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Serum (58 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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FTL Ferritin light chain (43324 Activities)

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gyrB DNA gyrase (2092 Activities)

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Ewingella americana (1 Activities)

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Peribacillus frigoritolerans (1 Activities)

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Mycobacterium leprae (477 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in aqueous base, 0.5 M NaOH (50 mg/ml), with heat as needed, yielding a clear, colorless solution, and formic acid. Partly miscible in water. Insoluble in DMF, and DMSO.
• Punto de inflamación (°C): >110°C(230°F)
• Punto de fusión (°C): 314-316°C
• Peso molecular: 261.230 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 261.064 Da
• Monoisotopic Mass: 261.064 Da
• Topological Polar Surface Area: 76.100 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 446.000
• 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

Referencias

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. Yuanjie Teng, Zhenni Wang, Shaohua Zuo, Xin Li, Yinxin Chen.  (2022)  Identification of antibiotic residues in aquatic products with surface-enhanced Raman scattering powered by 1-D convolutional neural networks.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:36549071] [10.1016/j.saa.2022.122195]

3. Wei Jiang, Wei-Rong Cui, Ru-Ping Liang, Jian-Ding Qiu.  (2021)  Difunctional covalent organic framework hybrid material for synergistic adsorption and selective removal of fluoroquinolone antibiotics.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:33609869] [10.1016/j.jhazmat.2021.125302]

4. Yijia Tang, Jianqiao Xu, Le Chen, Junlang Qiu, Yuan Liu, Gangfeng Ouyang.  (2017)  Rapid in vivo determination of fluoroquinolones in cultured puffer fish (Takifugu obscurus) muscle by solid-phase microextraction coupled with liquid chromatography-tandem mass spectrometry.  TALANTA,      [PMID:28842032] [10.1016/j.talanta.2017.07.066]

5. Wei Jiang, Run-Han Yan, Ru-Ping Liang, Jian-Ding Qiu.  (2024)  Double-lanthanide functionalized covalent organic framework hybrid material for the enhanced adsorption of fluoroquinolone antibiotics via synergistic effect.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2024.130753]

6. Song Shen, Yu-e Shi, Mingyuan Yin, Zhenguang Wang.  (2024)  Host–Guest Doping Modulated Afterglow Emission of Fluoroquinolones for Their Separation-Free Detection and Discrimination.  ANALYTICAL CHEMISTRY,      [PMID:38551637] [10.1021/acs.analchem.4c00412]

7. Guangxin Yang, Jingru Zhang, Junyu Zhang, Peng Wang, Wei Xia, Jun Wang, Xiaosheng Shen, Cong Kong.  (2025)  Utilization of wolfberry biomass waste-derived biochar as an efficient solid-phase extraction material for antibiotic detection in aquatic products.  FOOD CHEMISTRY,      [PMID:40617214] [10.1016/j.foodchem.2025.145390]

8. Jiayin Yang, Mingxiao Li, Xi Chen, Chao Song, Limin Fan, Liping Qiu, Dandan Li, Huimin Xu, Tiejun Li, Ying Huang, Shunlong Meng.  (2026)  Integrative Pharmacokinetic and Metabolomic Analyses Reveal the Underlying Mechanisms of Metabolic Regulation and Support the Safe Use of Oxolinic Acid in Micropterus salmoides.  Antioxidants,  15  (3): (283).  [PMID:] [10.3390/antiox15030283]