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Showing metabocard for Quinoline (HMDB0033731)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:29:27 UTC
Update Date2023-02-21 17:23:33 UTC
HMDB IDHMDB0033731
Secondary Accession Numbers
  • HMDB33731
Metabolite Identification
Common NameQuinoline
DescriptionQuinoline 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 found in alcoholic beverages. 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"
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033731 (Quinoline)

  Mrv1652304272018122D          

 10 11  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  2  6  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for HMDB0033731 (Quinoline)

HMDB0033731
     RDKit          3D
Quinoline
 17 18  0  0  0  0  0  0  0  0999 V2000
    2.2782    0.6663   -0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3985   -0.6056    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514   -1.3189    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080   -0.7662    0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1265   -1.4531    0.5836 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -0.9409    0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4939    0.3250   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3898    1.0711   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1457    0.5045   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0273    1.1928   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1837    1.2226   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3751   -1.0430    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -2.3079    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2546   -1.5178    0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5085    0.7050   -0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4615    2.0676   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035    2.1986   -0.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  1  1  0
  9  4  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
 10 17  1  0
M  END
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3D SDF for HMDB0033731 (Quinoline)

  Mrv1652304272018122D          

 10 11  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  2  6  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033731

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC=C2N=CC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H

> <INCHI_KEY>
SMWDFEZZVXVKRB-UHFFFAOYSA-N

> <FORMULA>
C9H7N

> <MOLECULAR_WEIGHT>
129.1586

> <EXACT_MASS>
129.057849229

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.94692341918513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
quinoline

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.1309004713333333

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.502796147983029

> <JCHEM_POLAR_SURFACE_AREA>
12.89

> <JCHEM_REFRACTIVITY>
39.979299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinch

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0033731 (Quinoline)

HMDB0033731
     RDKit          3D
Quinoline
 17 18  0  0  0  0  0  0  0  0999 V2000
    2.2782    0.6663   -0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3985   -0.6056    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514   -1.3189    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080   -0.7662    0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1265   -1.4531    0.5836 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -0.9409    0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4939    0.3250   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3898    1.0711   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1457    0.5045   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0273    1.1928   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1837    1.2226   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3751   -1.0430    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -2.3079    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2546   -1.5178    0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5085    0.7050   -0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4615    2.0676   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035    2.1986   -0.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  1  1  0
  9  4  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
 10 17  1  0
M  END
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PDB for HMDB0033731 (Quinoline)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -3.080   0.000   0.000  0.00  0.00           N+0
CONECT    1    2    4                                                       
CONECT    2    1    6                                                       
CONECT    3    5    7                                                       
CONECT    4    1    8                                                       
CONECT    5    3    8                                                       
CONECT    6    2    9                                                       
CONECT    7    3   10                                                       
CONECT    8    4    5    9                                                  
CONECT    9    6    8   10                                                  
CONECT   10    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0033731 (Quinoline)

COMPND    HMDB0033731
HETATM    1  C1  UNL     1       2.278   0.666  -0.245  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.398  -0.606   0.280  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.251  -1.319   0.559  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.008  -0.766   0.315  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.126  -1.453   0.584  1.00  0.00           N  
HETATM    6  C5  UNL     1      -2.345  -0.941   0.357  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.494   0.325  -0.166  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.390   1.071  -0.459  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.146   0.504  -0.210  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.027   1.193  -0.478  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.184   1.223  -0.462  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.375  -1.043   0.473  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.315  -2.308   0.967  1.00  0.00           H  
HETATM   14  H4  UNL     1      -3.255  -1.518   0.583  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.508   0.705  -0.336  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.462   2.068  -0.870  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.904   2.199  -0.893  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3   12
CONECT    3    4    4   13
CONECT    4    5    9
CONECT    5    6    6
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10
CONECT   10   17
END
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SMILES for HMDB0033731 (Quinoline)

C1=CC=C2N=CC=CC2=C1
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INCHI for HMDB0033731 (Quinoline)

InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Benzo[b]pyridineChEBI
ChinolinChEBI
Quinoline hydrochlorideMeSH
1-AzanaphthaleneHMDB
1-BenzazineHMDB
1-BenzineHMDB
2,3-BenzopyridineHMDB
benzo(b)PyridineHMDB
ChinoleineHMDB
ChinolineHMDB
FEMA 3470HMDB
LeucolHMDB
LeukolHMDB
QuinolinHMDB
Quinoline (8ci,9ci)HMDB
Chemical FormulaC9H7N
Average Molecular Weight129.1586
Monoisotopic Molecular Weight129.057849229
IUPAC Namequinoline
Traditional Namecinch
CAS Registry Number91-22-5
SMILES
C1=CC=C2N=CC=CC2=C1
InChI Identifier
InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
InChI KeySMWDFEZZVXVKRB-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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationEnvironmental roleBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-15.6 °CNot Available
Boiling Point239.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility6.11 mg/mL at 25 °CNot Available
LogP2.03Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011854
KNApSAcK IDC00026478
Chemspider ID6780
KEGG Compound IDC06413
BioCyc IDQUINOLINE
BiGG IDNot Available
Wikipedia LinkQuinoline
METLIN IDNot Available
PubChem Compound7047
PDB IDNot Available
ChEBI ID17362
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1583941
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:8216899 ]
  2. 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. [PubMed:6732221 ]
  3. 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. [PubMed:19066044 ]
  4. Musiol R, Serda M, Hensel-Bielowka S, Polanski J: Quinoline-based antifungals. Curr Med Chem. 2010;17(18):1960-73. [PubMed:20377510 ]
  5. Solomon VR, Lee H: Quinoline as a privileged scaffold in cancer drug discovery. Curr Med Chem. 2011;18(10):1488-508. [PubMed:21428893 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .