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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:57 UTC

HMDB ID

HMDB0015337

Secondary Accession Numbers

HMDB15337

Metabolite Identification

Common Name

Lomustine

Description

Lomustine is only found in individuals that have used or taken this drug. It is an alkylating agent of value against both hematologic malignancies and solid tumors. [PubChem]Lomustine is a highly lipophilic nitrosourea compound which undergoes hydrolysis in vivo to form reactive metabolites. These metabolites cause alkylation and cross-linking of DNA (at the O6 position of guanine-containing bases) and RNA, thus inducing cytotoxicity. Other biologic effects include inhibition of DNA synthesis and some cell cycle phase specificity. Nitrosureas generally lack cross-resistance with other alkylating agents. As lomustine is a nitrosurea, it may also inhibit several key processes such as carbamoylation and modification of cellular proteins.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0015337
     RDKit          3D
Lomustine
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.9086   -2.5063   -0.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -1.4493   -0.6632 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870   -0.1848   -0.0833 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0138    0.4699    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2744    0.0583    1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7487    0.7859    2.4122 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    0.3886    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058    1.5187    0.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -0.2945   -0.3483 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    0.2452   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674    0.4087   -1.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -0.0291   -1.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6981    0.5689   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1003   -0.1391    1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213   -0.6765    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8663    0.1286   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9628    1.5681    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    0.3771    2.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3400   -1.0446    1.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -1.2360   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656    1.2409    0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7018    1.4999   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.1733   -2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -1.1345   -1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6707    0.3824   -2.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3906    1.6336   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7974    0.5337   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.0158    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    0.4902    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -1.6764    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1621   -0.7386    1.6741 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
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

1206
  Mrv0541 02231215192D          

 15 15  0  0  0  0            999 V2000
    4.5080    2.6813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 13  2  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015337

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCCN(N=O)C(=O)NC1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)

> <INCHI_KEY>
GQYIWUVLTXOXAJ-UHFFFAOYSA-N

> <FORMULA>
C9H16ClN3O2

> <MOLECULAR_WEIGHT>
233.695

> <EXACT_MASS>
233.093104478

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.611412131908757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-chloroethyl)-1-cyclohexyl-3-nitrosourea

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.1574369699999996

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.302978190682751

> <JCHEM_PKA_STRONGEST_BASIC>
-5.349365921574837

> <JCHEM_POLAR_SURFACE_AREA>
61.77

> <JCHEM_REFRACTIVITY>
58.6506

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lomustine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015337
     RDKit          3D
Lomustine
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.9086   -2.5063   -0.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -1.4493   -0.6632 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870   -0.1848   -0.0833 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0138    0.4699    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2744    0.0583    1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7487    0.7859    2.4122 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    0.3886    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058    1.5187    0.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -0.2945   -0.3483 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    0.2452   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674    0.4087   -1.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -0.0291   -1.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6981    0.5689   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1003   -0.1391    1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213   -0.6765    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8663    0.1286   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9628    1.5681    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    0.3771    2.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3400   -1.0446    1.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -1.2360   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656    1.2409    0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7018    1.4999   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.1733   -2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -1.1345   -1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6707    0.3824   -2.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3906    1.6336   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7974    0.5337   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.0158    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    0.4902    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -1.6764    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1621   -0.7386    1.6741 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
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1206                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.415   5.005   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.081  -0.385   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414   4.235   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.414  -0.385   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.748   1.925   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.414   2.695   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.414  -1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -4.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -4.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -5.005   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   4.235   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   13                                                            
CONECT    3    6                                                            
CONECT    4    7   13                                                       
CONECT    5    6   13   14                                                  
CONECT    6    3    5                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
CONECT   13    2    4    5                                                  
CONECT   14    5   15                                                       
CONECT   15    1   14                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0015337
HETATM    1  O1  UNL     1       2.909  -2.506  -0.002  1.00  0.00           O  
HETATM    2  N1  UNL     1       2.901  -1.449  -0.663  1.00  0.00           N  
HETATM    3  N2  UNL     1       2.787  -0.185  -0.083  1.00  0.00           N  
HETATM    4  C1  UNL     1       4.014   0.470   0.330  1.00  0.00           C  
HETATM    5  C2  UNL     1       4.274   0.058   1.770  1.00  0.00           C  
HETATM    6 CL1  UNL     1       5.749   0.786   2.412  1.00  0.00          CL  
HETATM    7  C3  UNL     1       1.516   0.389   0.072  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.406   1.519   0.590  1.00  0.00           O  
HETATM    9  N3  UNL     1       0.364  -0.295  -0.348  1.00  0.00           N  
HETATM   10  C4  UNL     1      -0.979   0.245  -0.215  1.00  0.00           C  
HETATM   11  C5  UNL     1      -1.667   0.409  -1.528  1.00  0.00           C  
HETATM   12  C6  UNL     1      -3.110  -0.029  -1.427  1.00  0.00           C  
HETATM   13  C7  UNL     1      -3.698   0.569  -0.150  1.00  0.00           C  
HETATM   14  C8  UNL     1      -3.100  -0.139   1.054  1.00  0.00           C  
HETATM   15  C9  UNL     1      -1.721  -0.676   0.729  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.866   0.129  -0.297  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.963   1.568   0.213  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.357   0.377   2.342  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.340  -1.045   1.790  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.478  -1.236  -0.778  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.866   1.241   0.260  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.702   1.500  -1.792  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.176  -0.173  -2.347  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.218  -1.134  -1.448  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.671   0.382  -2.297  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.391   1.634  -0.139  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.797   0.534  -0.165  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.748  -1.016   1.260  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.101   0.490   1.960  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.814  -1.676   0.287  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.162  -0.739   1.674  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3
CONECT    3    4    7
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    7    8    8    9
CONECT    9   10   20
CONECT   10   11   15   21
CONECT   11   12   22   23
CONECT   12   13   24   25
CONECT   13   14   26   27
CONECT   14   15   28   29
CONECT   15   30   31
END

HMDB0015337
     RDKit          3D
Lomustine
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.9086   -2.5063   -0.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -1.4493   -0.6632 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870   -0.1848   -0.0833 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0138    0.4699    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2744    0.0583    1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7487    0.7859    2.4122 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    0.3886    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058    1.5187    0.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -0.2945   -0.3483 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    0.2452   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674    0.4087   -1.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -0.0291   -1.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6981    0.5689   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1003   -0.1391    1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213   -0.6765    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8663    0.1286   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9628    1.5681    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    0.3771    2.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3400   -1.0446    1.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -1.2360   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656    1.2409    0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7018    1.4999   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.1733   -2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -1.1345   -1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6707    0.3824   -2.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3906    1.6336   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7974    0.5337   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.0158    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    0.4902    1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -1.6764    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1621   -0.7386    1.6741 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
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea	ChEBI
1-(2-Chloroethyl)-3-cyclohexylnitrosourea	ChEBI
Belustine	ChEBI
CCNU	ChEBI
Cecenu	ChEBI
CeeNU	ChEBI
Chloroethylcyclohexylnitrosourea	ChEBI
CINU	ChEBI
Cyclohexyl chloroethyl nitrosourea	ChEBI
Lomustina	ChEBI
Lomustinum	ChEBI
N-(2-Chloroethyl)-n'-cyclohexyl-N-nitrosourea	ChEBI
Gleostine	Kegg
Bristol-myers squibb brand OF lomustine	HMDB
Rhône-poulenc rorer brand OF lomustine	HMDB
Medac brand OF lomustine	HMDB
Bristol myers squibb brand OF lomustine	HMDB
Rhône poulenc rorer brand OF lomustine	HMDB
Lomustine medac brand	HMDB

Chemical Formula

C₉H₁₆ClN₃O₂

Average Molecular Weight

233.695

Monoisotopic Molecular Weight

233.093104478

IUPAC Name

3-(2-chloroethyl)-1-cyclohexyl-3-nitrosourea

Traditional Name

lomustine

CAS Registry Number

13010-47-4

SMILES

ClCCN(N=O)C(=O)NC1CCCCC1

InChI Identifier

InChI=1S/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)

InChI Key

GQYIWUVLTXOXAJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic carbonic acids and derivatives

Sub Class

Ureas

Direct Parent

Nitrosoureas

Alternative Parents

Substituents

Nitrosourea
Semicarbazide
Nitrosamide
Organic n-nitroso compound
Organic nitroso compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alkyl chloride
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Organic nitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:6520 )
N-nitrosoureas (CHEBI:6520 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015337)
Membrane (HMDB: HMDB0015337)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	88 - 90 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.76 g/L	Not Available
LogP	3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.76 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.16	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.3	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.65 m³·mol⁻¹	ChemAxon
Polarizability	23.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	156.869	30932474
DeepCCS	[M-H]-	154.483	30932474
DeepCCS	[M-2H]-	189.22	30932474
DeepCCS	[M+Na]+	164.511	30932474
AllCCS	[M+H]+	150.5	32859911
AllCCS	[M+H-H2O]+	147.0	32859911
AllCCS	[M+NH4]+	153.8	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	151.4	32859911
AllCCS	[M+Na-2H]-	152.2	32859911
AllCCS	[M+HCOO]-	153.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lomustine	ClCCN(N=O)C(=O)NC1CCCCC1	2256.4	Standard polar	33892256
Lomustine	ClCCN(N=O)C(=O)NC1CCCCC1	1538.2	Standard non polar	33892256
Lomustine	ClCCN(N=O)C(=O)NC1CCCCC1	1834.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lomustine,1TMS,isomer #1	C[Si](C)(C)N(C(=O)N(CCCl)N=O)C1CCCCC1	1882.2	Semi standard non polar	33892256
Lomustine,1TMS,isomer #1	C[Si](C)(C)N(C(=O)N(CCCl)N=O)C1CCCCC1	1897.4	Standard non polar	33892256
Lomustine,1TMS,isomer #1	C[Si](C)(C)N(C(=O)N(CCCl)N=O)C1CCCCC1	2790.9	Standard polar	33892256
Lomustine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N(CCCl)N=O)C1CCCCC1	2123.2	Semi standard non polar	33892256
Lomustine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N(CCCl)N=O)C1CCCCC1	2094.4	Standard non polar	33892256
Lomustine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N(CCCl)N=O)C1CCCCC1	2910.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lomustine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-8900000000-edefb2c60fb3a4723f1b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lomustine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 10V, Positive-QTOF	splash10-003r-9870000000-c1e5d9089d0ca3ebe990	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 20V, Positive-QTOF	splash10-004j-9600000000-553a8bea32ca95f8b8c9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 40V, Positive-QTOF	splash10-03di-9000000000-237df2753e3c79610270	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 10V, Negative-QTOF	splash10-05aj-4940000000-52228cb236f776094d55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 20V, Negative-QTOF	splash10-0002-9520000000-f52d4c064b87d135bcab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 40V, Negative-QTOF	splash10-0002-9100000000-c986da9a3b5f2025b30c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 10V, Positive-QTOF	splash10-03e9-9410000000-3c91b816a1fd60d9fb41	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 20V, Positive-QTOF	splash10-03e9-9100000000-e9795a3320548e7e0520	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 40V, Positive-QTOF	splash10-001i-9000000000-13ca0d883f27e08e4efe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 10V, Negative-QTOF	splash10-001i-3190000000-21d4dc32f394af73cd0d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 20V, Negative-QTOF	splash10-001i-9000000000-99ed100e7c6291a96d1b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lomustine 40V, Negative-QTOF	splash10-001i-9000000000-7fe5321df11e6429faf4	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01206	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01206	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01206

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3813

KEGG Compound ID

C07079

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lomustine

METLIN ID

Not Available

PubChem Compound

3950

PDB ID

Not Available

ChEBI ID

6520

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Lomustine (HMDB0015337)

MOL for HMDB0015337 (Lomustine)

3D MOL for HMDB0015337 (Lomustine)

3D SDF for HMDB0015337 (Lomustine)

3D-SDF for HMDB0015337 (Lomustine)

PDB for HMDB0015337 (Lomustine)

3D PDB for HMDB0015337 (Lomustine)

SMILES for HMDB0015337 (Lomustine)

INCHI for HMDB0015337 (Lomustine)

Structure for HMDB0015337 (Lomustine)

3D Structure for HMDB0015337 (Lomustine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References