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Showing NP-Card for 3-Hydroxyquinoline (NP0083442)

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Record Information
Version2.0
Created at2022-04-29 04:29:15 UTC
Updated at2022-04-29 04:29:15 UTC
NP-MRD IDNP0083442
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxyquinoline
Description3-Hydroxyquinoline 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. 3-Hydroxyquinoline is found in Ruta montana . 3-Hydroxyquinoline was first documented in 2010 (PMID: 20112454). Based on a literature review a small amount of articles have been published on 3-Hydroxyquinoline (PMID: 23047245) (PMID: 31070920) (PMID: 28471077) (PMID: 26810790).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083442 (3-Hydroxyquinoline)


  Mrv1652304292206292D          

 11 12  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0083442 (3-Hydroxyquinoline)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
    3.5134    0.3768    0.7044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841    0.4686    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7879    1.5867   -0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4915    1.6583   -0.7234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172    0.6910   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7443    0.8127   -0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6709   -0.1598   -0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2741   -1.2770    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9575   -1.4374    0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612   -0.4424    0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2860   -0.5274    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1346   -0.0878    0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896    2.3723   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885    1.7146   -1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848   -0.0058   -0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0066   -2.0216    0.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -2.3117    1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5700   -1.4101    1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  2  1  0
 10  5  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 11 18  1  0
M  END
Download

3D SDF for NP0083442 (3-Hydroxyquinoline)


  Mrv1652304292206292D          

 11 12  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CN=C2C=CC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO/c11-8-5-7-3-1-2-4-9(7)10-6-8/h1-6,11H

> <INCHI_KEY>
IQQDNMHUOLMLNJ-UHFFFAOYSA-N

> <FORMULA>
C9H7NO

> <MOLECULAR_WEIGHT>
145.161

> <EXACT_MASS>
145.052763849

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.931847032098341

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
quinolin-3-ol

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.8273351496666665

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.670686605180503

> <JCHEM_PKA_STRONGEST_BASIC>
4.387739496856151

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
41.9602

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-quinolinol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0083442 (3-Hydroxyquinoline)

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PDB for NP0083442 (3-Hydroxyquinoline)
HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0083442 (3-Hydroxyquinoline)
Download
SMILES for NP0083442 (3-Hydroxyquinoline)
OC1=CN=C2C=CC=CC2=C1
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INCHI for NP0083442 (3-Hydroxyquinoline)
InChI=1S/C9H7NO/c11-8-5-7-3-1-2-4-9(7)10-6-8/h1-6,11H
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H7NO
Average Mass145.1610 Da
Monoisotopic Mass145.05276 Da
IUPAC Namequinolin-3-ol
Traditional Name3-quinolinol
CAS Registry NumberNot Available
SMILES
OC1=CN=C2C=CC=CC2=C1
InChI Identifier
InChI=1S/C9H7NO/c11-8-5-7-3-1-2-4-9(7)10-6-8/h1-6,11H
InChI KeyIQQDNMHUOLMLNJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ruta montanaPlant
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
    • 

  • Hydroxypyridine
    • 

  • Benzenoid
    • 

  • Pyridine
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.95ALOGPS
logP1.83ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)4.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.96 m³·mol⁻¹ChemAxon
Polarizability14.93 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00052145  
Chemspider ID10898  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Hydroxyquinoline  
METLIN IDNot Available
PubChem Compound11376  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Shaaban KA, Shepherd MD, Ahmed TA, Nybo SE, Leggas M, Rohr J: Pyramidamycins A-D and 3-hydroxyquinoline-2-carboxamide; cytotoxic benzamides from Streptomyces sp. DGC1. J Antibiot (Tokyo). 2012 Dec;65(12):615-22. doi: 10.1038/ja.2012.81. Epub 2012 Oct 10. [PubMed:23047245  ] 
  2. Dhiman AK, Chandra D, Kumar R, Sharma U: Catalyst-Free Synthesis of 2-Anilinoquinolines and 3-Hydroxyquinolines via Three-Component Reaction of Quinoline N-Oxides, Aryldiazonium Salts, and Acetonitrile. J Org Chem. 2019 Jun 7;84(11):6962-6969. doi: 10.1021/acs.joc.9b00739. Epub 2019  May 23. [PubMed:31070920  ] 
  3. Hattori H, Yokoshima S, Fukuyama T: Total Syntheses of Aurachins A and B. Angew Chem Int Ed Engl. 2017 Jun 6;56(24):6980-6983. doi: 10.1002/anie.201702204. Epub 2017 May 4. [PubMed:28471077  ] 
  4. Felczak A, Bernat P, Rozalska S, Lisowska K: Quinoline biodegradation by filamentous fungus Cunninghamella elegans and adaptive modifications of the fungal membrane composition. Environ Sci Pollut Res Int. 2016 May;23(9):8872-80. doi: 10.1007/s11356-016-6116-4. Epub 2016 Jan 26. [PubMed:26810790  ] 
  5. Furuya T, Kino K: Regioselective oxidation of indole- and quinolinecarboxylic acids by cytochrome P450 CYP199A2. Appl Microbiol Biotechnol. 2010 Feb;85(6):1861-8. doi: 10.1007/s00253-009-2207-1. [PubMed:20112454  ]