Quinoline
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Basic Info
| Common Name | Quinoline(F03771) |
| 2D Structure | |
| Description | Quinoline is found in alcoholic beverages. Quinoline is an alkaloid from various plant species including Mentha species. Also present in cocoa, black tea and scotch whiskey. Quinoline is a flavouring ingredient Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline is mainly used as a building block to other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[citation needed] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name Assert. Quinoline has been shown to exhibit catabolic, anti-microbial, anti-tumor, anti-fungal and anti-cancer functions (A7755, A7756, A7757, A7759, A7760). |
| FRCD ID | F03771 |
| CAS Number | 91-22-5 |
| PubChem CID | 7047 |
| Formula | C9H7N |
| IUPAC Name | quinoline |
| InChI Key | SMWDFEZZVXVKRB-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H |
| Canonical SMILES | C1=CC=C2C(=C1)C=CC=N2 |
| Isomeric SMILES | C1=CC=C2C(=C1)C=CC=N2 |
| Wikipedia | Quinoline |
| Synonyms |
Benzo[b]pyridine
QUINOLINE
91-22-5
Chinolin
Chinoline
1-Benzazine
Quinolin
1-Azanaphthalene
Chinoleine
Leucol
|
| Classifies |
Plant Toxin
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Quinolines and derivatives |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Quinolines and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Quinoline - Benzenoid - Pyridine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as quinolines and derivatives. These are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 129.162 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 111 |
| Monoisotopic Mass | 129.058 |
| Exact Mass | 129.058 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9866 |
| Human Intestinal Absorption | HIA+ | 0.9961 |
| Caco-2 Permeability | Caco2+ | 0.7659 |
| P-glycoprotein Substrate | Non-substrate | 0.7617 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9517 |
| Non-inhibitor | 0.9754 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7613 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6206 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8313 |
| CYP450 2D6 Substrate | Non-substrate | 0.8351 |
| CYP450 3A4 Substrate | Non-substrate | 0.7555 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9188 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5260 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.5667 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8774 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8837 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6283 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9575 |
| Non-inhibitor | 0.8709 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.9312 |
| Fish Toxicity | High FHMT | 0.5681 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8189 |
| Honey Bee Toxicity | High HBT | 0.5608 |
| Biodegradation | Not ready biodegradable | 0.8030 |
| Acute Oral Toxicity | III | 0.6050 |
| Carcinogenicity (Three-class) | Non-required | 0.6901 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8427 | LogS |
| Caco-2 Permeability | 1.7335 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2813 | LD50, mol/kg |
| Fish Toxicity | 1.7656 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2758 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| In vitro toxicity and in silico docking analysis of two novel selective AH-receptor modulators. | Toxicol In Vitro | 2018 Oct | 29908305 |
| DNA damage protection by bulk and nano forms of quercetin in lymphocytes of patients with chronic obstructive pulmonary disease exposed to the food mutagen 2-amino-3-methylimidazo [4,5-f]quinolone (IQ). | Environ Res | 2018 Oct | 29807314 |
| TQOPEN (N,N,N',N'-Tetrakis(2-quinolylmethyl)-3-oxa-1,5-pentanediamine) Family as Heptadentate Fluorescent Cd2+ Sensors. | Inorg Chem | 2017 Jul 3 | 28621934 |
| Evolution of metabolic divergence in Pseudomonas aeruginosa during long-term infection facilitates a proto-cooperative interspecies interaction. | ISME J | 2016 Jun | 26684729 |
| Grafting polyethylenimine with quinoline derivatives for targeted imaging ofintracellular Zn(2+) and logic gate operations. | Mater Sci Eng C Mater Biol Appl | 2016 Dec 1 | 27612748 |
| Study of the cytotoxic/toxic potential of the novel anticancer selenodiazoloquinolone on fibroblast cells and 3D skin model. | Interdiscip Toxicol | 2016 Dec | 28652854 |
| In silico and in vitro genotoxicity evaluation of descarboxyl levofloxacin, an impurity in levofloxacin. | Drug Chem Toxicol | 2014 Jul | 24224725 |
| Interstitial modification of palladium nanoparticles with boron atoms as a green catalyst for selective hydrogenation. | Nat Commun | 2014 Dec 19 | 25523894 |
| Biofunctional constituent isolated from Citrullus colocynthis fruits andstructure-activity relationships of its analogues show acaricidal andinsecticidal efficacy. | J Agric Food Chem | 2014 Aug 27 | 25110971 |
| Synthesis of quinoline derivatives of tetrahydrocurcumin and zingerone andevaluation of their antioxidant and antibacterial attributes. | Food Chem | 2013 Jan 15 | 23122110 |
| Alternaria toxins: Altertoxin II is a much stronger mutagen and DNA strand breaking mycotoxin than alternariol and its methyl ether in cultured mammalian cells. | Toxicol Lett | 2012 Oct 2 | 22902351 |
| Electrochemical studies of quinine in surfactant media using hanging mercury dropelectrode: a cyclic voltammetric study. | Colloids Surf B Biointerfaces | 2012 Oct 1 | 22659207 |
| [Determination of sixteen food additives in beverage by capillary zoneelectrophoresis]. | Se Pu | 2012 Jul | 23189674 |
| Effect of cigarette menthol content on mainstream smoke emissions. | Chem Res Toxicol | 2011 Oct 17 | 21888394 |
| Glove accumulation of pesticide residues for strawberry harvester exposureassessment. | Bull Environ Contam Toxicol | 2011 Jun | 21503692 |
| Toxicokinetics of the food-toxin IQ in human placental perfusion is not affected by ABCG2 or xenobiotic metabolism. | Placenta | 2010 Jul | 20570348 |
| Antimutagenic effects of lycopene and tomato purée. | J Med Food | 2010 Dec | 20874227 |
| Reduced frequency of atopic dermatitis in quinoline-allergic patients: the'hapten-atopy hypothesis'. | Contact Dermatitis | 2008 May | 18416760 |
| 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) attenuates LPS-induced IL-8 expression by decreasing mRNA stability in THP-1 cells. | Toxicol Lett | 2008 Mar 15 | 18281166 |
| In vitro inhibitory activity of probiotic spore-forming bacilli against genotoxins. | Lett Appl Microbiol | 2008 Mar | 18194161 |
Targets
- General Function:
- Thrombin receptor activity
- Specific Function:
- High affinity receptor for activated thrombin coupled to G proteins that stimulate phosphoinositide hydrolysis. May play a role in platelets activation and in vascular development.
- Gene Name:
- F2R
- Uniprot ID:
- P25116
- Molecular Weight:
- 47439.83 Da
References
- Clasby MC, Chackalamannil S, Czarniecki M, Doller D, Eagen K, Greenlee WJ, Lin Y, Tsai H, Xia Y, Ahn HS, Agans-Fantuzzi J, Boykow G, Chintala M, Foster C, Bryant M, Lau J: Discovery and synthesis of a novel series of quinoline-based thrombin receptor (PAR-1) antagonists. Bioorg Med Chem Lett. 2006 Mar 15;16(6):1544-8. Epub 2005 Dec 27. [16380251 ]
- General Function:
- Glycine n-methyltransferase activity
- Specific Function:
- Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
- Gene Name:
- GNMT
- Uniprot ID:
- Q14749
- Molecular Weight:
- 32742.0 Da
- Mechanism of Action:
- Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis.
References
- Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
- Gene Name:
- CYP2D6
- Uniprot ID:
- P10635
- Molecular Weight:
- 55768.94 Da
References
- Strobl GR, von Kruedener S, Stockigt J, Guengerich FP, Wolff T: Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies. J Med Chem. 1993 Apr 30;36(9):1136-45. [8487254 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
- Mechanism of Action:
- Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis.
References
- Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity).Isoform 1 is critical for hindlimb motor control and for the differentiation of amacrine and horizontal cells in the retina. Regulates the expression of PTF1A synergistically with FOXN4 (By similarity).
- Gene Name:
- RORB
- Uniprot ID:
- Q92753
- Molecular Weight:
- 53219.385 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]