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Showing NP-Card for Cotinine N-oxide (NP0086773)

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Record Information
Version2.0
Created at2022-05-11 16:30:35 UTC
Updated at2022-05-11 16:30:35 UTC
NP-MRD IDNP0086773
Secondary Accession NumbersNone
Natural Product Identification
Common NameCotinine N-oxide
DescriptionCotinine N-oxide belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. An N-alkylpyrrolidine that is nicotine in which the methylene hydrogens at position 2 on the pyrrolidine ring have been replaced by an oxo group and the pyridine nitrogen converted to the corresponding N-oxide. Cotinine N-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Cotinine N-oxide was first documented in 1992 (PMID: 1478978). In humans, cotinine N-oxide is involved in nicotine metabolism pathway (PMID: 15472033) (PMID: 8294547) (PMID: 16359169).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086773 (Cotinine N-oxide)


  Mrv0541 02231219072D          

 14 15  0  0  1  0            999 V2000
    8.7332   -6.3752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2569   -7.0375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5233   -6.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7332   -7.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4319   -7.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5233   -7.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1855   -6.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -6.3287    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.4777   -5.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0137   -6.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0137   -7.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7822   -7.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -7.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6274   -5.4982    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  9  1  1  0  0  0  0
  4  2  1  0  0  0  0
  2  5  1  1  0  0  0
  6  3  1  0  0  0  0
  7  3  2  0  0  0  0
  6  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 10  8  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
M  CHG  2   8   1  14  -1
M  END
Download

3D MOL for NP0086773 (Cotinine N-oxide)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -1.1871   -1.9404    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957   -0.6812    0.2246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -0.0574    0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8021   -0.5705    0.8262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7056    1.3147   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1914    1.5593   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894    0.1753   -0.5987 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7518    0.0834   -0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932    0.0764    0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722   -0.0146    1.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5120   -0.0991    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -0.0905   -1.2013 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.7839   -0.1744   -2.2981 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6130   -0.0022   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -2.3970    0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502   -1.8476    1.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953   -2.7059    0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2647    2.0558    0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772    1.2758   -1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795    2.3378   -0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035    1.7324    0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090    0.0228   -1.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6499    0.1415    1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006   -0.0199    2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841   -0.1711    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2668   -0.0033   -2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  7  8  1  0
  8 14  2  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  3  2  1  0
  9  8  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  7 22  1  6
  6 20  1  0
  6 21  1  0
  5 18  1  0
  5 19  1  0
 14 26  1  0
 11 25  1  0
 10 24  1  0
  9 23  1  0
M  CHG  2  12   1  13  -1
M  END
Download

3D SDF for NP0086773 (Cotinine N-oxide)


  Mrv0541 02231219072D          

 14 15  0  0  1  0            999 V2000
    8.7332   -6.3752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2569   -7.0375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5233   -6.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7332   -7.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4319   -7.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5233   -7.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1855   -6.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -6.3287    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.4777   -5.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0137   -6.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0137   -7.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7822   -7.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -7.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6274   -5.4982    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  9  1  1  0  0  0  0
  4  2  1  0  0  0  0
  2  5  1  1  0  0  0
  6  3  1  0  0  0  0
  7  3  2  0  0  0  0
  6  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 10  8  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
M  CHG  2   8   1  14  -1
M  END
> <DATABASE_ID>
NP0086773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1

> <INCHI_KEY>
CIPULDKLIIVIER-VIFPVBQESA-N

> <FORMULA>
C10H12N2O2

> <MOLECULAR_WEIGHT>
192.2145

> <EXACT_MASS>
192.089877638

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.49733863167793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate

> <ALOGPS_LOGP>
-0.66

> <JCHEM_LOGP>
-1.0495223999999999

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.8049121441667914

> <JCHEM_POLAR_SURFACE_AREA>
45.77

> <JCHEM_REFRACTIVITY>
52.970000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086773 (Cotinine N-oxide)

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PDB for NP0086773 (Cotinine N-oxide)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      16.302 -11.900   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      15.413 -13.137   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.777 -12.378   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.302 -14.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.873 -13.137   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.777 -13.917   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.013 -11.467   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.552 -11.814   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      15.825 -10.426   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.092 -11.814   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.092 -14.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.793 -13.137   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.552 -14.481   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.505 -10.263   0.000  0.00  0.00           O-1
CONECT    1    2    3    9                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1    6    7                                                  
CONECT    4    2    6                                                       
CONECT    5    2   10   11                                                  
CONECT    6    3    4                                                       
CONECT    7    3                                                            
CONECT    8   10   12   14                                                  
CONECT    9    1                                                            
CONECT   10    5    8                                                       
CONECT   11    5   13                                                       
CONECT   12    8   13                                                       
CONECT   13   11   12                                                       
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0086773 (Cotinine N-oxide)
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SMILES for NP0086773 (Cotinine N-oxide)
CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1
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INCHI for NP0086773 (Cotinine N-oxide)
InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
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View in JSmol
Synonyms
ValueSource
(-)-Cotinine N-oxideChEBI
(5S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinoneChEBI
(S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinoneChEBI
(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone N-oxideChEBI
3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olateChEBI
Cotinine-N-oxideChEBI
3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olic acidGenerator
Cotinine-1-N-oxideHMDB
Chemical FormulaC10H12N2O2
Average Mass192.2145 Da
Monoisotopic Mass192.08988 Da
IUPAC Name3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate
Traditional Name3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate
CAS Registry NumberNot Available
SMILES
CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1
InChI Identifier
InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
InChI KeyCIPULDKLIIVIER-VIFPVBQESA-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyridines and derivatives  
Sub ClassPyrrolidinylpyridines  
Direct ParentPyrrolidinylpyridines  
Alternative Parents
Substituents
  • Pyrrolidinylpyridine
    • 

  • Alkaloid or derivatives
    • 

  • Pyridinium
    • 

  • Pyrrolidone
    • 

  • 2-pyrrolidone
    • 

  • N-alkylpyrrolidine
    • 

  • Pyrrolidine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Heteroaromatic compound
    • 

  • Lactam
    • 

  • Carboxamide group
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP-0.66ALOGPS
logP-1ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)0.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.97 m³·mol⁻¹ChemAxon
Polarizability19.5 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001411  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022606  
KNApSAcK IDNot Available
Chemspider ID7991264  
KEGG Compound IDNot Available
BioCyc IDCPD-3185  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6227  
PubChem Compound9815514  
PDB IDNot Available
ChEBI ID89087  
Good Scents IDNot Available
References
General References
  1. Xu X, Iba MM, Weisel CP: Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry. Clin Chem. 2004 Dec;50(12):2323-30. Epub 2004 Oct 7. [PubMed:15472033  ] 
  2. Zuccaro P, Altieri I, Rosa M, Passa AR, Pichini S, Ricciarello G, Pacifici R: Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Nov 24;621(2):257-61. doi: 10.1016/0378-4347(93)80103-b. [PubMed:8294547  ] 
  3. Jacob P 3rd, Shulgin AT, Yu L, Benowitz NL: Determination of the nicotine metabolite trans-3'-hydroxycotinine in urine of smokers using gas chromatography with nitrogen-selective detection or selected ion monitoring. J Chromatogr. 1992 Dec 2;583(2):145-54. doi: 10.1016/0378-4347(92)80547-4. [PubMed:1478978  ] 
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