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Showing metabocard for N'-nitrosonornicotine (HMDB0041940)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:04 UTC
Update Date2023-02-21 17:29:04 UTC
HMDB IDHMDB0041940
Secondary Accession Numbers
  • HMDB41940
Metabolite Identification
Common NameN'-nitrosonornicotine
DescriptionN'-nitrosonornicotine, also known as NNN, 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. N'-nitrosonornicotine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. N'-nitrosonornicotine is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review very few articles have been published on N'-nitrosonornicotine.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041940 (N'-nitrosonornicotine)

  Mrv0541 09131211492D          

 13 14  0  0  0  0            999 V2000
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -0.2916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  7  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
M  END
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3D MOL for HMDB0041940 (N'-nitrosonornicotine)

HMDB0041940
     RDKit          3D
N'-nitrosonornicotine
 24 25  0  0  0  0  0  0  0  0999 V2000
   -0.7646    2.9356    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    1.7300    1.7764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    0.7611    0.8019 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167    0.8620   -0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4504   -0.5614   -0.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421   -1.3479   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103   -0.4972    0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -0.3008    0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2694    0.5575   -0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076    0.6989   -0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353   -0.0224   -0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815   -0.8689    0.7710 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778   -1.0135    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1837    1.2264    0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8890    1.4648   -1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5735   -0.6075   -1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -1.0111   -0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -2.3364    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410   -1.5586   -1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -0.9790    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    1.0952   -1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9612    1.3541   -1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5865    0.1136   -0.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6345   -1.6948    1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  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  3  1  0
 13  8  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 13 24  1  0
M  END
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3D SDF for HMDB0041940 (N'-nitrosonornicotine)

  Mrv0541 09131211492D          

 13 14  0  0  0  0            999 V2000
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -0.2916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  7  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041940

> <DATABASE_NAME>
hmdb

> <SMILES>
O=NN1CCCC1C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2

> <INCHI_KEY>
XKABJYQDMJTNGQ-UHFFFAOYSA-N

> <FORMULA>
C9H11N3O

> <MOLECULAR_WEIGHT>
177.2031

> <EXACT_MASS>
177.090211989

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.127519060420216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1-nitrosopyrrolidin-2-yl)pyridine

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.0109790493333333

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.786847453716268

> <JCHEM_POLAR_SURFACE_AREA>
45.56

> <JCHEM_REFRACTIVITY>
49.71739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitrosonornicotine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0041940 (N'-nitrosonornicotine)

HMDB0041940
     RDKit          3D
N'-nitrosonornicotine
 24 25  0  0  0  0  0  0  0  0999 V2000
   -0.7646    2.9356    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    1.7300    1.7764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    0.7611    0.8019 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167    0.8620   -0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4504   -0.5614   -0.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421   -1.3479   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103   -0.4972    0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -0.3008    0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2694    0.5575   -0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076    0.6989   -0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353   -0.0224   -0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815   -0.8689    0.7710 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778   -1.0135    1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1837    1.2264    0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8890    1.4648   -1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5735   -0.6075   -1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -1.0111   -0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -2.3364    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410   -1.5586   -1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -0.9790    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    1.0952   -1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9612    1.3541   -1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5865    0.1136   -0.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6345   -1.6948    1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  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  3  1  0
 13  8  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 13 24  1  0
M  END
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PDB for HMDB0041940 (N'-nitrosonornicotine)

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.906  -2.485   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.381  -1.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.366  -2.485   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       6.469   3.735   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.425  -0.544   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.890  -1.020   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       1.281  -1.575   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    8                                                       
CONECT    4    2    9                                                       
CONECT    5    1   10                                                       
CONECT    6    2   12                                                       
CONECT    7    8   10                                                       
CONECT    8    3    7    9                                                  
CONECT    9    4    8   12                                                  
CONECT   10    5    7                                                       
CONECT   11   12   13                                                       
CONECT   12    6    9   11                                                  
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0041940 (N'-nitrosonornicotine)

COMPND    HMDB0041940
HETATM    1  O1  UNL     1      -0.765   2.936   1.468  1.00  0.00           O  
HETATM    2  N1  UNL     1      -0.967   1.730   1.776  1.00  0.00           N  
HETATM    3  N2  UNL     1      -1.225   0.761   0.802  1.00  0.00           N  
HETATM    4  C1  UNL     1      -2.217   0.862  -0.247  1.00  0.00           C  
HETATM    5  C2  UNL     1      -2.450  -0.561  -0.732  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.242  -1.348  -0.269  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.510  -0.497   0.720  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.911  -0.301   0.352  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.269   0.557  -0.664  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.608   0.699  -0.961  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.535  -0.022  -0.231  1.00  0.00           C  
HETATM   12  N3  UNL     1       3.182  -0.869   0.771  1.00  0.00           N  
HETATM   13  C9  UNL     1       1.878  -1.014   1.068  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.184   1.226   0.194  1.00  0.00           H  
HETATM   15  H2  UNL     1      -1.889   1.465  -1.106  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.574  -0.607  -1.830  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.361  -1.011  -0.283  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.545  -2.336   0.134  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.541  -1.559  -1.113  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.610  -0.979   1.715  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.515   1.095  -1.201  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.961   1.354  -1.744  1.00  0.00           H  
HETATM   23  H10 UNL     1       4.586   0.114  -0.493  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.635  -1.695   1.871  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3
CONECT    3    4    7
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20
CONECT    8    9    9   13
CONECT    9   10   21
CONECT   10   11   11   22
CONECT   11   12   23
CONECT   12   13   13
CONECT   13   24
END
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SMILES for HMDB0041940 (N'-nitrosonornicotine)

O=NN1CCCC1C1=CN=CC=C1
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INCHI for HMDB0041940 (N'-nitrosonornicotine)

InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
NNNKegg
N-NitrosonornicotineHMDB
NitrosonornicotineHMDB
N-Nitrosonor-nicotineHMDB
N'-nitrosonornicotine, (+-)-isomerHMDB
N'-nitrosonornicotine, (S)-isomerHMDB
Chemical FormulaC9H11N3O
Average Molecular Weight177.2031
Monoisotopic Molecular Weight177.090211989
IUPAC Name3-(1-nitrosopyrrolidin-2-yl)pyridine
Traditional Namenitrosonornicotine
CAS Registry Number16543-55-8
SMILES
O=NN1CCCC1C1=CN=CC=C1
InChI Identifier
InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2
InChI KeyXKABJYQDMJTNGQ-UHFFFAOYSA-N
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
  • Heteroaromatic compound
  • Pyrrolidine
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point47 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID25973
KEGG Compound IDC16452
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Nitrosonornicotine
METLIN IDNot Available
PubChem Compound27919
PDB IDNot Available
ChEBI ID80502
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available