Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:59:16 UTC
Update Date2014-12-24 20:22:27 UTC
Accession NumberT3D0634
Identification
Common NameQuinoline
ClassSmall Molecule
DescriptionQuinoline 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 (4, 5, 6, 7, 8).
Compound Type
  • Aromatic Hydrocarbon
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pesticide
  • Plant Toxin
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
Thumb
Synonyms
Synonym
1-Azanaphthalene
1-Benzazine
1-Benzine
2,3-Benzopyridine
Benzo(b)pyridine
Benzo[b]pyridine
Chinoleine
Chinolin
Chinoline
Leucol
Leukol
Quinolin
Chemical FormulaC9H7N
Average Molecular Mass129.159 g/mol
Monoisotopic Mass129.058 g/mol
CAS Registry Number91-22-5
IUPAC Namequinoline
Traditional Namecinch
SMILESC1=CC=C2N=CC=CC2=C1
InChI IdentifierInChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
InChI KeyInChIKey=SMWDFEZZVXVKRB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassNot Available
Direct ParentQuinolines and derivatives
Alternative Parents
Substituents
  • Quinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless solid.
Experimental Properties
PropertyValue
Melting Point-15.6°C
Boiling Point238°C (460.4°F)
Solubility6.11 mg/mL at 25°C
LogP2.03
Predicted Properties
PropertyValueSource
Water Solubility3.37 g/LALOGPS
logP2.19ALOGPS
logP2.13ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.98 m³·mol⁻¹ChemAxon
Polarizability13.95 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-6650a64dcfaff97a384fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9700000000-162da149cecb7471177eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-589a1fb16b83c4fe8115View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-f63ba1bba58ccc63c20aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-06d1e2a8216798421e17View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-6650a64dcfaff97a384fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9700000000-162da149cecb7471177eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-589a1fb16b83c4fe8115View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-f63ba1bba58ccc63c20aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-06d1e2a8216798421e17View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-0900000000-5bfb659404cb36aa304fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-f80d7ca98d120817a55cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-027cf5e71116c5fcb4b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-b503a364d204d8e6ac8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-8900000000-49aa8f9641f21e97fc43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-25969cc68eb743f7f3dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7ca73e074935b2add2f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-a45f6683fe6d4b0b16aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7026ebf0519b2fba0024View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-1900000000-09e171e9467e40b551d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fai-4900000000-7b17c392210401ee485dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fba-9700000000-581ee9456c67170a0520View in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-6596d88125ed21410c6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-6c1f93bf41d02c99ce73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-3900000000-7293ce5372993b70ea55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f7d71396a8498e54005aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-f7d71396a8498e54005aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-678317c07cf462bbdfa9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-4900000000-f18da8f2e791614f0c9aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (11) ; inhalation (11)
Mechanism of ToxicityThe ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. 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. (11, 12, 2, 3)
MetabolismPAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (11)
Toxicity ValuesLD50: 331 mg/kg (Oral, Rat) (9) LD50: 540 mg/kg (Dermal, Rabbit) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC. IARC has evaluated related PAHs (13).
Uses/SourcesPAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (11)
Minimum Risk LevelNot Available
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (11)
SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)
TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (11)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB33731
PubChem Compound ID7047
ChEMBL IDCHEMBL14474
ChemSpider ID6780
KEGG IDC06413
UniProt IDNot Available
OMIM ID
ChEBI ID17362
BioCyc IDRS-TETRAHYDROBENZYLISOQUINOLINE
CTD IDC037219
Stitch IDQuinoline
PDB IDNot Available
ACToR ID1750
Wikipedia LinkQuinoline
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Santodonato J, Howard P, Basu D: Health and ecological assessment of polynuclear aromatic hydrocarbons. J Environ Pathol Toxicol. 1981 Sep;5(1):1-364. [7310260 ]
  2. 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 ]
  3. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  4. Ruger A, Schwarz G, Lingens F: Microbial metabolism of quinoline and related compounds. XIX. Degradation of 4-methylquinoline and quinoline by Pseudomonas putida K1. Biol Chem Hoppe Seyler. 1993 Jul;374(7):479-88. [8216899 ]
  5. Van Caekenberghe DL, Pattyn SR: In vitro activity of ciprofloxacin compared with those of other new fluorinated piperazinyl-substituted quinoline derivatives. Antimicrob Agents Chemother. 1984 Apr;25(4):518-21. [6732221 ]
  6. Xu XD, Hu XR, Yang JS: [Review of studies on active components of antitumor medicinal plants]. Zhongguo Zhong Yao Za Zhi. 2008 Sep;33(17):2073-81. [19066044 ]
  7. Musiol R, Serda M, Hensel-Bielowka S, Polanski J: Quinoline-based antifungals. Curr Med Chem. 2010;17(18):1960-73. [20377510 ]
  8. Solomon VR, Lee H: Quinoline as a privileged scaffold in cancer drug discovery. Curr Med Chem. 2011;18(10):1488-508. [21428893 ]
  9. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  11. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  12. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
  13. International Agency for Research on Cancer. 2010. Some Non-heterocyclic Polycyclic Aromatic Hydrocarbons and Some Related Exposures. IARC monograph, volume 92. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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
References
  1. 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 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. 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 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
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
References
  1. 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 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory>1000 uMNot AvailableBindingDB 50047015
References
  1. 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:
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
  1. 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:
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC505.38 uMATG_RORb_TRANSAttagene
References
  1. 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 ]