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Showing NP-Card for Cotinine (NP0000004)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-17 21:37:42 UTC
NP-MRD IDNP0000004
Natural Product DOIhttps://doi.org/10.57994/1244
Secondary Accession NumbersNone
Natural Product Identification
Common NameCotinine
DescriptionCotinine is an alkaloid found in tobacco (Nicotiana tabacum). Cotinine 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. It is also the predominant human metabolite of nicotine (when nicotine is inhaled or absorbed). In humans, about 70 to 80% of nicotine that is inhaled or absorbed is converted to cotinine. This transformation involves two steps. The first is mediated by a cytochrome P450 system (mainly CYP2A6 and CYP2B6) to produce nicotine iminium ion. The second step is catalyzed by aldehyde oxidase (AOX). A number of cotinine metabolites have also been structurally characterized. Indeed, it appears that most of the reported urinary metabolites of nicotine are derived from cotinine. Cotinine is widely used as a biomarker for exposure to tobacco smoke. Cotinine has an in vivo half-life of approximately 20 hours, and is typically detectable for several days (up to one week) after the use of tobacco. Similar to nicotine, cotinine binds to, activates, and desensitizes neuronal nicotinic acetylcholine receptors, though at much lower potency in comparison. It has demonstrated nootropic and antipsychotic-like effects in animal models. Cotinine treatment has also been shown to reduce depression, anxiety, and fear-related behavior as well as memory impairment in animal models of depression, PTSD, and Alzheimer's disease.
Structure
Data?1664554194
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000004 (Cotinine)


  Mrv1652305201900032D          

 13 14  0  0  0  0            999 V2000
   11.4710   -6.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9190   -7.1529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0984   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7628   -7.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3757   -8.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0902   -7.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8438   -8.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6859   -6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0984   -5.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6859   -4.9231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -4.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4485   -5.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
Download

3D MOL for NP0000004 (Cotinine)

HMDB0001046
     RDKit          3D
Cotinine
 25 26  0  0  0  0  0  0  0  0999 V2000
   -1.1908    1.9464   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3240    0.5577   -0.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910   -0.0809   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6191    0.5393   -1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4681   -1.5384   -0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0795   -1.6064    0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676   -0.5222   -0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740   -0.2377   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    0.9154   -0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9164    1.1708    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606    0.2816    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -0.8366    1.2039 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589   -1.1031    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616    2.5166   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1112    2.3725    0.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    2.1715    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512   -1.9266    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -2.0395   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252   -1.2873    1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256   -2.5929    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3376   -0.8483   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746    1.6666   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4098    2.0704   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5818    0.4420    1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2270   -2.0309    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7  2  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
M  END
Download

3D SDF for NP0000004 (Cotinine)


  Mrv1652305201900032D          

 13 14  0  0  0  0            999 V2000
   11.4710   -6.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9190   -7.1529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0984   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7628   -7.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3757   -8.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0902   -7.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8438   -8.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6859   -6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0984   -5.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6859   -4.9231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -4.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4485   -5.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(CCC1=O)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3

> <INCHI_KEY>
UIKROCXWUNQSPJ-UHFFFAOYSA-N

> <FORMULA>
C10H12N2O

> <MOLECULAR_WEIGHT>
176.2151

> <EXACT_MASS>
176.094963016

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.57458933125395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
0.2106345276666668

> <ALOGPS_LOGS>
-0.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.789340020074378

> <JCHEM_POLAR_SURFACE_AREA>
33.2

> <JCHEM_REFRACTIVITY>
49.2805

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-cotinine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000004 (Cotinine)

HMDB0001046
     RDKit          3D
Cotinine
 25 26  0  0  0  0  0  0  0  0999 V2000
   -1.1908    1.9464   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3240    0.5577   -0.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910   -0.0809   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6191    0.5393   -1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4681   -1.5384   -0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0795   -1.6064    0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676   -0.5222   -0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740   -0.2377   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    0.9154   -0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9164    1.1708    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606    0.2816    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -0.8366    1.2039 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589   -1.1031    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616    2.5166   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1112    2.3725    0.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    2.1715    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512   -1.9266    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -2.0395   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252   -1.2873    1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256   -2.5929    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3376   -0.8483   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746    1.6666   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4098    2.0704   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5818    0.4420    1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2270   -2.0309    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7  2  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
M  END
Download

PDB for NP0000004 (Cotinine)

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0      21.413 -12.207   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      20.382 -13.352   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      18.850 -13.191   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.224 -14.598   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.368 -15.628   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.702 -14.858   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      22.108 -15.485   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.080 -11.857   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.850 -10.524   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      18.080  -9.190   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      16.540  -9.190   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.771 -10.524   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.540 -11.857   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6                                                            
CONECT    8    3    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
Download

3D PDB for NP0000004 (Cotinine)

COMPND    HMDB0001046
HETATM    1  C1  UNL     1      -1.191   1.946  -0.060  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.324   0.558  -0.364  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.591  -0.081  -0.638  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.619   0.539  -1.050  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.468  -1.538  -0.358  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.079  -1.606   0.298  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.368  -0.522  -0.480  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.974  -0.238  -0.037  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.611   0.915  -0.419  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.916   1.171   0.029  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.561   0.282   0.843  1.00  0.00           C  
HETATM   12  N2  UNL     1       2.921  -0.837   1.204  1.00  0.00           N  
HETATM   13  C10 UNL     1       1.659  -1.103   0.783  1.00  0.00           C  
HETATM   14  H1  UNL     1      -1.062   2.517  -0.993  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.111   2.372   0.421  1.00  0.00           H  
HETATM   16  H3  UNL     1      -0.380   2.172   0.682  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.251  -1.927   0.293  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.402  -2.039  -1.344  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.225  -1.287   1.351  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.626  -2.593   0.200  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.338  -0.848  -1.539  1.00  0.00           H  
HETATM   22  H9  UNL     1       1.175   1.667  -1.061  1.00  0.00           H  
HETATM   23  H10 UNL     1       3.410   2.070  -0.271  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.582   0.442   1.217  1.00  0.00           H  
HETATM   25  H12 UNL     1       1.227  -2.031   1.127  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6   17   18
CONECT    6    7   19   20
CONECT    7    8   21
CONECT    8    9    9   13
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   12   24
CONECT   12   13   13
CONECT   13   25
END
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SMILES for NP0000004 (Cotinine)

CN1C(CCC1=O)C1=CN=CC=C1
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INCHI for NP0000004 (Cotinine)

InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3
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View in JSmol
Synonyms
ValueSource
Cotinine(15% OF the dose)HMDB
(-)-CotinineHMDB
(S)-(-)-CotinineHMDB
(S)-CotinineHMDB
CotininaHMDB
CotininumHMDB
S-(-)-CotinineHMDB
Chemical FormulaC10H12N2O
Average Mass176.2151 Da
Monoisotopic Mass176.09496 Da
IUPAC Name1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
Traditional Name(-)-cotinine
CAS Registry Number486-56-6
SMILES
CN1C(CCC1=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3
InChI KeyUIKROCXWUNQSPJ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-07View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-07View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-11-07View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
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
Carica papaya L.FooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Haloxylon persicumLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Nicotiana alataLOTUS Database
Nicotiana tabacumLOTUS Database
Nicotiana tabacum (L.)KNApSAcK Database
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
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Lactam
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point41 °Chttps://pubchem.ncbi.nlm.nih.gov/compound/854019#section=Melting-Point
Boiling Point210 - 211 °Chttps://pubchem.ncbi.nlm.nih.gov/compound/854019#section=Boiling-Point
Water Solubility1000https://pubchem.ncbi.nlm.nih.gov/compound/854019#section=Solubility
LogP0.07Li, N. Y., Li, Y., & Gorrod, J. W. (1992). Determination of partition coefficients and ionisation constants of(S)(-)-nicotine and certain metabolites. Medical Science Research[MED. SCI. RES.]., 20(23).
Predicted Properties
PropertyValueSource
Water Solubility117 g/LALOGPS
logP0.39ALOGPS
logP0.21ChemAxon
logS-0.18ALOGPS
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area33.2 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.28 m³·mol⁻¹ChemAxon
Polarizability18.57 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001046
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004716
KNApSAcK IDC00034470
Chemspider ID395
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCotinine
METLIN ID1531
PubChem Compound408
PDB IDNot Available
ChEBI ID127762
Good Scents IDNot Available
References
General References
  1. Bentley MC, Abrar M, Kelk M, Cook J, Phillips K: Validation of an assay for the determination of cotinine and 3-hydroxycotinine in human saliva using automated solid-phase extraction and liquid chromatography with tandem mass spectrometric detection. J Chromatogr B Biomed Sci Appl. 1999 Feb 19;723(1-2):185-94. [PubMed:10080645 ]
  2. Urakawa N, Nagata T, Kudo K, Kimura K, Imamura T: Simultaneous determination of nicotine and cotinine in various human tissues using capillary gas chromatography/mass spectrometry. Int J Legal Med. 1994;106(5):232-6. [PubMed:8068568 ]
  3. Poppe WA, Peeters R, Drijkoningen M, Ide PS, Daenens P, Lauweryns JM, Van Assche FA: Cervical cotinine and macrophage-Langerhans cell density in the normal human uterine cervix. Gynecol Obstet Invest. 1996;41(4):253-9. [PubMed:8793496 ]
  4. Jacqz-Aigrain E, Zhang D, Maillard G, Luton D, Andre J, Oury JF: Maternal smoking during pregnancy and nicotine and cotinine concentrations in maternal and neonatal hair. BJOG. 2002 Aug;109(8):909-11. [PubMed:12197371 ]
  5. Gwent SH, Wilson JF, Tsanaclis LM, Wicks JF: Time course of appearance of cotinine in human beard hair after a single dose of nicotine. Ther Drug Monit. 1995 Apr;17(2):195-8. [PubMed:7624910 ]
  6. Dobek D, Karmowski A, Sobiech KA, Terpilowski L, Mis-Michalek M: Average quantitative concentration of cotinine within the system pregnant woman-baby. Arch Immunol Ther Exp (Warsz). 1998;46(1):59-61. [PubMed:9510948 ]
  7. Torano JS, van Kan HJ: Simultaneous determination of the tobacco smoke uptake parameters nicotine, cotinine and thiocyanate in urine, saliva and hair, using gas chromatography-mass spectrometry for characterisation of smoking status of recently exposed subjects. Analyst. 2003 Jul;128(7):838-43. [PubMed:12894819 ]
  8. Knight JM, Eliopoulos C, Klein J, Greenwald M, Koren G: Passive smoking in children. Racial differences in systemic exposure to cotinine by hair and urine analysis. Chest. 1996 Feb;109(2):446-50. [PubMed:8620720 ]
  9. Hatsukami DK, Jensen J, Brauer LH, Mooney M, Schulte S, Sofuoglu M, Pentel PR: Lack of effect of 5HT3 antagonist in mediating subjective and behavioral responses to cotinine. Pharmacol Biochem Behav. 2003 Apr;75(1):1-7. [PubMed:12759107 ]
  10. Laskowska-Klita T, Chelchowska M, Leibschang J: [Concentrations of cotinine in serum and urine of smoking pregnant women and in placenta and umbilical cord blood]. Przegl Lek. 2005;62(10):1007-9. [PubMed:16521941 ]
  11. Authors unspecified: Nicotine absorption by workers harvesting green tobacco. Lancet. 1975 Mar 1;1(7905):478-80. [PubMed:46956 ]
  12. Tutka P, Wielosz M, Zatonski W: Exposure to environmental tobacco smoke and children health. Int J Occup Med Environ Health. 2002;15(4):325-35. [PubMed:12608620 ]
  13. Paszkowski T: [Concentration gradient of cotinine between blood serum and preovulatory follicular fluid]. Ginekol Pol. 1998 Dec;69(12):1131-6. [PubMed:10224789 ]
  14. Poppe WA, Peeters R, Daenens P, Ide PS, Van Assche FA: Tobacco smoking and the uterine cervix: cotinine in blood, urine and cervical fluid. Gynecol Obstet Invest. 1995;39(2):110-4. [PubMed:7737579 ]
  15. Istvan JA, Lee WW, Buist AS, Connett JE: Relation of salivary cotinine to blood pressure in middle-aged cigarette smokers. Am Heart J. 1999 May;137(5):928-31. [PubMed:10220643 ]
  16. Nafstad P, Botten G, Hagen JA, Zahlsen K, Nilsen OG, Silsand T, Kongerud J: Comparison of three methods for estimating environmental tobacco smoke exposure among children aged between 12 and 36 months. Int J Epidemiol. 1995 Feb;24(1):88-94. [PubMed:7797361 ]
  17. Eliopoulos C, Klein J, Chitayat D, Greenwald M, Koren G: Nicotine and cotinine in maternal and neonatal hair as markers of gestational smoking. Clin Invest Med. 1996 Aug;19(4):231-42. [PubMed:8853571 ]
  18. Eliopoulos C, Klein J, Koren G: Validation of self-reported smoking by analysis of hair for nicotine and cotinine. Ther Drug Monit. 1996 Oct;18(5):532-6. [PubMed:8885115 ]
  19. Wilson SE, Kahn RS, Khoury J, Lanphear BP: Racial differences in exposure to environmental tobacco smoke among children. Environ Health Perspect. 2005 Mar;113(3):362-7. [PubMed:15743729 ]
  20. Kintz P: Gas chromatographic analysis of nicotine and cotinine in hair. J Chromatogr. 1992 Sep 16;580(1-2):347-53. [PubMed:1400830 ]