8-Hydroxy-5-nitroquinoline - ≥97% , CAS No.4008-48-4

CAS: 4008-48-4 Cat. No.: H107536 Molecular Weight: 190.16 Beilstein Registry Number: 21(5)3,297 EC Number: 223-662-4

GRADE & PURITY ≥97%

Synonyms

5-Nitro-8-hydroxyquinoline | 8-Quinolinol, 5-nitro- | Nitroxolina | W-106391 | 5-Nitroquinolin-8-ol, 96% | HNQ | Nitroxolinum | DB01422 | Nitrohydroxyquinoline | 5-Nitro-quinolin-8-ol | 5-nitroquinolin-8-ol | NITROXOLINE [MART.] | NCGC00160664-03 | Nitrox

Storage

Argon charged,Room temperature

Shipped In

Normal

Specifications

Synonyms

5-Nitro-8-hydroxyquinoline | 8-Quinolinol, 5-nitro- | Nitroxolina | W-106391 | 5-Nitroquinolin-8-ol, 96% | HNQ | Nitroxolinum | DB01422 | Nitrohydroxyquinoline | 5-Nitro-quinolin-8-ol | 5-nitroquinolin-8-ol | NITROXOLINE [MART.] | NCGC00160664-03 | Nitrox

Specifications & Purity

≥97%

Biochemical and Physiological Mechanisms

8-Hydroxy-5-nitroquinoline is an effective anti-microbial and anti-cancer agent. It is an effective drug for the treatment of urinary tract infections due to gram negative bacilli.

Storage

Argon charged, Room temperature

Shipped In

Normal

Action Type

INHIBITOR

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 488182572
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488182572
• Canonical Smiles: C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]
• IUPAC Name: 5-nitroquinolin-8-ol
• InChIKey: RJIWZDNTCBHXAL-UHFFFAOYSA-N
• INCHI: 1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
• Isomeric SMILES: C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]
• WGK Germany: 3
• RTECS: VC8225000
• Molecular Weight: 190.16
• Beilstein: 21(5)3,297
• Reaxy-Rn: 166146
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=166146&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives
      • Subclass Nitroquinolines and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: Nitroquinolines and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitroquinolines and derivatives
• Alternative Parents: 8-hydroxyquinolines Nitroaromatic compounds 1-hydroxy-2-unsubstituted benzenoids Pyridines and derivatives Heteroaromatic compounds Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Nitroquinoline - 8-hydroxyquinoline - Nitroaromatic compound - 1-hydroxy-2-unsubstituted benzenoid - Pyridine - Benzenoid - Heteroaromatic compound - C-nitro compound - Organic nitro compound - Organic oxoazanium - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Hydrocarbon derivative - Organic zwitterion - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as nitroquinolines and derivatives. These are compounds containing a nitro group attached to a quinoline moiety.
• External Descriptors: C-nitro compound - monohydroxyquinoline

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)

BRD4 Tchem Bromodomain-containing protein 4 (2 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

HSP90AA1 Tchem Heat shock protein HSP 90-alpha (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PTGS2 Tclin Prostaglandin G/H synthase 2 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

METAP2 Tchem Methionine aminopeptidase 2 (2 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

F2 Tclin Thrombin (11687 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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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VDR Tclin Vitamin D receptor (26531 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 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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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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COMT Tclin Catechol O-methyltransferase (404 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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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 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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HRH1 Tclin Histamine H1 receptor (7573 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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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 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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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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METAP1 Tchem Methionine aminopeptidase 1 (614 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSB Tchem Cathepsin B (3822 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

METAP2 Tchem Methionine aminopeptidase 2 (1512 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)

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HSP90AA1 Tchem Heat shock protein HSP 90-alpha (4115 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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Associated Targets(non-human)

Pde4d Phosphodiesterase 4D (4 Activities)

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Hdac6 Histone deacetylase 6 (222 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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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Enterococcus faecium (13803 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Enterococcus faecalis (29875 Activities)

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Plasmodium falciparum (966862 Activities)

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Candida albicans (78123 Activities)

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Rattus norvegicus (775804 Activities)

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Alpha trans-inducing protein (VP16) (945 Activities)

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dnaB Replicative DNA helicase (15 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapt Microtubule-associated protein tau (6 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rorc Nuclear receptor ROR-gamma (89407 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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ATP-dependent molecular chaperone HSP82 (2186 Activities)

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NS1 Nonstructural protein 1 (33327 Activities)

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recA Protein RecA (2211 Activities)

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HSP90 (947 Activities)

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Burkholderia pseudomallei (576 Activities)

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SARS-CoV-2 (38078 Activities)

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Burkholderia thailandensis (182 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: alcohol: very slightly soluble diethyl ether: very slightly soluble hydrochloric acid: freely soluble (hot)
• Sensitivity: air sensitive，light sensitive
• Melt Point(°C): 180°C
• Molecular Weight: 190.160 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 190.038 Da
• Monoisotopic Mass: 190.038 Da
• Topological Polar Surface Area: 78.900 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 229.000
• 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. Yi Sun, Junfeng Su, Amjad Ali, Tinglin Huang, Shuai Zhang, Yitian Min.  (2022)  Enhanced nitrate and cadmium removal performance at low carbon to nitrogen ratio through immobilized redox mediator granules and functional strains in a bioreactor.  CHEMOSPHERE,      [PMID:36402354] [10.1016/j.chemosphere.2022.137255]

2. Yong Cheng, Feifei Sun, Qichun Feng, Qiang Zhao, Yinghua Zhou.  (2017)  In situ synthesis of AgNPs@Ag(I)-AMTD metal-organic gel composite and its catalytic properties.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2017.02.040]