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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014436

Secondary Accession Numbers

HMDB14436

Metabolite Identification

Common Name

Chlorambucil

Description

Chlorambucil, also known as ambochlorin or chloraminophen, belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom. Chlorambucil is a drug which is used for treatment of chronic lymphatic (lymphocytic) leukemia, childhood minimal-change nephrotic syndrome, and malignant lymphomas including lymphosarcoma, giant follicular lymphoma, hodgkin's disease, non-hodgkin's lymphomas, and waldenström’s macroglobulinemia. Chlorambucil is a moderately basic compound (based on its pKa). Chlorambucil is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound.

Structure

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

HMDB0014436
     RDKit          3D
Chlorambucil
 38 38  0  0  0  0  0  0  0  0999 V2000
    6.8313    0.2804   -1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6005    0.1289   -0.9806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9386   -0.7806   -1.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224    0.9345   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3717    0.5923   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748    1.3472    0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812    0.8671    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -0.2219    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -0.6876    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911   -0.0855    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -0.5454   -0.2377 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081    0.0067    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    1.0751    1.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812    1.7500    2.4083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9816   -1.5269   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3912   -2.8565   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9576   -2.8856    0.0801 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    1.0072   -0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851    1.4898   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126   -0.9256   -2.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1294    0.7536    1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789    2.0323   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526   -0.4976    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940    0.7817   -1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266    1.0941    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5464    2.4407    0.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743   -0.7632    1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0643   -1.5402    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6428    0.5635   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5254   -0.7153    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991    0.6708    2.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379    1.9104    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8125   -1.1443   -1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -1.5871   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184   -3.5504   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -3.2714   -0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.5114   -1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6838    2.3474   -0.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 10 18  1  0
 18 19  2  0
 19  7  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
M  END

291
  Mrv0541 02231214342D          

 19 19  0  0  0  0            999 V2000
    2.3645    3.8405    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.8405    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.5847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4 19  2  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  2  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 14  2  0  0  0  0
  8 15  1  0  0  0  0
  9 16  1  0  0  0  0
 10 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014436

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)

> <INCHI_KEY>
JCKYGMPEJWAADB-UHFFFAOYSA-N

> <FORMULA>
C14H19Cl2NO2

> <MOLECULAR_WEIGHT>
304.212

> <EXACT_MASS>
303.079284271

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.982298958361955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
3.9371549819999987

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.455549351160488

> <JCHEM_PKA_STRONGEST_BASIC>
1.7171649065281474

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
79.6828

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorambucil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014436
     RDKit          3D
Chlorambucil
 38 38  0  0  0  0  0  0  0  0999 V2000
    6.8313    0.2804   -1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6005    0.1289   -0.9806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9386   -0.7806   -1.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224    0.9345   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3717    0.5923   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748    1.3472    0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812    0.8671    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -0.2219    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -0.6876    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911   -0.0855    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -0.5454   -0.2377 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081    0.0067    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    1.0751    1.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812    1.7500    2.4083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9816   -1.5269   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3912   -2.8565   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9576   -2.8856    0.0801 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    1.0072   -0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851    1.4898   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126   -0.9256   -2.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1294    0.7536    1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789    2.0323   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526   -0.4976    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940    0.7817   -1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266    1.0941    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5464    2.4407    0.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743   -0.7632    1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0643   -1.5402    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6428    0.5635   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5254   -0.7153    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991    0.6708    2.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379    1.9104    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8125   -1.1443   -1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -1.5871   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184   -3.5504   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -3.2714   -0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.5114   -1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6838    2.3474   -0.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 10 18  1  0
 18 19  2  0
 19  7  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 291                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.414   7.169   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       9.748   7.169   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       4.414  -6.691   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -4.381   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.081   4.089   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.081   2.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -2.071   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -2.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   4.859   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   4.859   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   1.779   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   1.779   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748   0.239   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   0.239   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -4.381   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748   6.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415   6.399   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -5.151   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    6   10   11                                                  
CONECT    6    5   12   13                                                  
CONECT    7    8    9                                                       
CONECT    8    7   14   15                                                  
CONECT    9    7   16                                                       
CONECT   10    5   17                                                       
CONECT   11    5   18                                                       
CONECT   12    6   14                                                       
CONECT   13    6   15                                                       
CONECT   14    8   12                                                       
CONECT   15    8   13                                                       
CONECT   16    9   19                                                       
CONECT   17    1   10                                                       
CONECT   18    2   11                                                       
CONECT   19    3    4   16                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0014436
HETATM    1  O1  UNL     1       6.831   0.280  -1.032  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.601   0.129  -0.981  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.939  -0.781  -1.817  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.822   0.934  -0.007  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.372   0.592  -0.134  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.475   1.347   0.808  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.081   0.867   0.520  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.614  -0.222   1.219  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.670  -0.688   0.971  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.491  -0.086   0.041  1.00  0.00           C  
HETATM   11  N1  UNL     1      -2.828  -0.545  -0.238  1.00  0.00           N  
HETATM   12  C9  UNL     1      -3.908   0.007   0.508  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.423   1.075   1.491  1.00  0.00           C  
HETATM   14 CL1  UNL     1      -4.781   1.750   2.408  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -2.982  -1.527  -1.250  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.391  -2.857  -0.733  1.00  0.00           C  
HETATM   17 CL2  UNL     1      -4.958  -2.886   0.080  1.00  0.00          CL  
HETATM   18  C13 UNL     1      -0.990   1.007  -0.644  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.285   1.490  -0.415  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.313  -0.926  -2.749  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.129   0.754   1.046  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.979   2.032  -0.215  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.253  -0.498   0.127  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.994   0.782  -1.170  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.727   1.094   1.860  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.546   2.441   0.663  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.174  -0.763   1.965  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.064  -1.540   1.505  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.643   0.563  -0.147  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.525  -0.715   1.068  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.699   0.671   2.203  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.938   1.910   0.947  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.812  -1.144  -1.935  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.099  -1.587  -1.937  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.418  -3.550  -1.620  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.595  -3.271  -0.071  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.602   1.511  -1.386  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.684   2.347  -0.949  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    8   19
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   18
CONECT   11   12   15
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   18   19   19   37
CONECT   19   38
END

HMDB0014436
     RDKit          3D
Chlorambucil
 38 38  0  0  0  0  0  0  0  0999 V2000
    6.8313    0.2804   -1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6005    0.1289   -0.9806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9386   -0.7806   -1.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224    0.9345   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3717    0.5923   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748    1.3472    0.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812    0.8671    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -0.2219    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -0.6876    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911   -0.0855    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -0.5454   -0.2377 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081    0.0067    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    1.0751    1.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812    1.7500    2.4083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9816   -1.5269   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3912   -2.8565   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9576   -2.8856    0.0801 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    1.0072   -0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851    1.4898   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126   -0.9256   -2.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1294    0.7536    1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789    2.0323   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526   -0.4976    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940    0.7817   -1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266    1.0941    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5464    2.4407    0.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743   -0.7632    1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0643   -1.5402    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6428    0.5635   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5254   -0.7153    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991    0.6708    2.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379    1.9104    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8125   -1.1443   -1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -1.5871   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184   -3.5504   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -3.2714   -0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.5114   -1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6838    2.3474   -0.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 10 18  1  0
 18 19  2  0
 19  7  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(p-Bis(beta-chloroethyl)aminophenyl)butyric acid	ChEBI
4-[p-[Bis(2-chloroethyl)amino]phenyl]butyric acid	ChEBI
Ambochlorin	ChEBI
Chloraminophen	ChEBI
gamma-[p-Di(2-chloroethyl)aminophenyl]butyric acid	ChEBI
Leukeran	ChEBI
N,N-Di-2-chloroethyl-gamma-p-aminophenylbutyric acid	ChEBI
Phenylbutyric acid nitrogen mustard	ChEBI
4-(p-Bis(b-chloroethyl)aminophenyl)butyrate	Generator
4-(p-Bis(b-chloroethyl)aminophenyl)butyric acid	Generator
4-(p-Bis(beta-chloroethyl)aminophenyl)butyrate	Generator
4-(p-Bis(β-chloroethyl)aminophenyl)butyrate	Generator
4-(p-Bis(β-chloroethyl)aminophenyl)butyric acid	Generator
4-[p-[Bis(2-chloroethyl)amino]phenyl]butyrate	Generator
g-[p-Di(2-chloroethyl)aminophenyl]butyrate	Generator
g-[p-Di(2-chloroethyl)aminophenyl]butyric acid	Generator
gamma-[p-Di(2-chloroethyl)aminophenyl]butyrate	Generator
Γ-[p-di(2-chloroethyl)aminophenyl]butyrate	Generator
Γ-[p-di(2-chloroethyl)aminophenyl]butyric acid	Generator
N,N-Di-2-chloroethyl-g-p-aminophenylbutyrate	Generator
N,N-Di-2-chloroethyl-g-p-aminophenylbutyric acid	Generator
N,N-Di-2-chloroethyl-gamma-p-aminophenylbutyrate	Generator
N,N-Di-2-chloroethyl-γ-p-aminophenylbutyrate	Generator
N,N-Di-2-chloroethyl-γ-p-aminophenylbutyric acid	Generator
Phenylbutyrate nitrogen mustard	Generator
Chlocambucil	HMDB
Chloraminophene	HMDB
Chlorbutin	HMDB
Chlorbutine	HMDB
Chloroambucil	HMDB
Chlorobutin	HMDB
Chlorobutine	HMDB
Lympholysin	HMDB
4-(Bis(2-chloroethyl)amino)benzenebutanoic acid	HMDB
Amboclorin	HMDB
Glaxo wellcome brand OF chlorambucil	HMDB
GlaxoSmithKline brand OF chlorambucil	HMDB
N,N-Di-(2-chloroethyl)-p-aminophenylbutyric acid	HMDB
Wellcome brand OF chlorambucil	HMDB

Chemical Formula

C₁₄H₁₉Cl₂NO₂

Average Molecular Weight

304.212

Monoisotopic Molecular Weight

303.079284271

IUPAC Name

4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid

Traditional Name

chlorambucil

CAS Registry Number

305-03-3

SMILES

OC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl

InChI Identifier

InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)

InChI Key

JCKYGMPEJWAADB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen mustard compounds

Alternative Parents

Substituents

Aniline or substituted anilines
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Nitrogen mustard
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Amino acid
Tertiary amine
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alkyl chloride
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:28830 )
monocarboxylic acid (CHEBI:28830 )
organochlorine compound (CHEBI:28830 )
aromatic amine (CHEBI:28830 )
nitrogen mustard (CHEBI:28830 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014436)
Membrane (HMDB: HMDB0014436)

Source

Exogenous

Exogenous (HMDB: HMDB0014436)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	65 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.077 g/L	Not Available
LogP	3.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	168.701	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000700

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.077 g/L	ALOGPS
logP	3.81	ALOGPS
logP	3.94	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	1.72	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	79.68 m³·mol⁻¹	ChemAxon
Polarizability	31.98 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]+	165.341	30932474
DeepCCS	[M-H]-	162.983	30932474
DeepCCS	[M-2H]-	195.905	30932474
DeepCCS	[M+Na]+	171.435	30932474
AllCCS	[M+H]+	165.1	32859911
AllCCS	[M+H-H2O]+	162.0	32859911
AllCCS	[M+NH4]+	167.9	32859911
AllCCS	[M+Na]+	168.7	32859911
AllCCS	[M-H]-	169.2	32859911
AllCCS	[M+Na-2H]-	169.6	32859911
AllCCS	[M+HCOO]-	170.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorambucil	OC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl	3575.0	Standard polar	33892256
Chlorambucil	OC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl	2477.9	Standard non polar	33892256
Chlorambucil	OC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl	2455.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chlorambucil,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1	2456.6	Semi standard non polar	33892256
Chlorambucil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1	2706.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorambucil GC-MS (Non-derivatized) - 70eV, Positive	splash10-066u-2790000000-bf4786edba412b2ccaae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorambucil GC-MS (1 TMS) - 70eV, Positive	splash10-024i-5393000000-3be6fe379684458bfa85	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorambucil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-2491000000-ddb7d5da8316562dba36	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorambucil LC-ESI-qTof , Positive-QTOF	splash10-004i-0002900000-472e293a011d716bb5a8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorambucil , positive-QTOF	splash10-0zfr-0519000000-1bca00472dfc8c30a465	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 10V, Positive-QTOF	splash10-0udr-0096000000-3899963778fe2e6e88de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 20V, Positive-QTOF	splash10-08g0-3591000000-6ae3349b3f490c58310d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 40V, Positive-QTOF	splash10-0j4i-6920000000-15483700b73ee5d5c44b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 10V, Negative-QTOF	splash10-0udi-0039000000-b8ff9ca35aa22b00bd35	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 20V, Negative-QTOF	splash10-0uxr-1193000000-7606e0823853c0c258ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 40V, Negative-QTOF	splash10-052f-9540000000-f5720e555315984712a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 10V, Negative-QTOF	splash10-001i-9004000000-788a1a6f740556f91441	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 20V, Negative-QTOF	splash10-001i-9000000000-724cdb1db65352c21f6c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 40V, Negative-QTOF	splash10-001i-9100000000-58ace4115f9b048a722e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 10V, Positive-QTOF	splash10-0udr-0098000000-d1dce37c9e184d7829de	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 20V, Positive-QTOF	splash10-00kr-0091000000-f4d0cc5c505d1414f7cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorambucil 40V, Positive-QTOF	splash10-014m-1920000000-59f8073bfe41e45f2bdb	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB00291	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00291	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

DB00291

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2607

KEGG Compound ID

C06900

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorambucil

METLIN ID

Not Available

PubChem Compound

2708

PDB ID

Not Available

ChEBI ID

28830

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

Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7. [PubMed:11114313 ]
Yang K, Tan J, Wu T: Alkylating agents for Waldenstrom's macroglobulinaemia. Cochrane Database Syst Rev. 2009 Jan 21;(1):CD006719. doi: 10.1002/14651858.CD006719.pub3. [PubMed:19160296 ]

Enzymes

Enzyme Details

1. Glutathione S-transferase P

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:: GSTP1
Uniprot ID:: P09211
Molecular weight:: 23355.625

References

Parker LJ, Ciccone S, Italiano LC, Primavera A, Oakley AJ, Morton CJ, Hancock NC, Bello ML, Parker MW: The anti-cancer drug chlorambucil as a substrate for the human polymorphic enzyme glutathione transferase P1-1: kinetic properties and crystallographic characterisation of allelic variants. J Mol Biol. 2008 Jun 27;380(1):131-44. doi: 10.1016/j.jmb.2008.04.066. Epub 2008 May 4. [PubMed:18511072 ]
Zhang J, Lou YJ: Relationship between activation of microsomal glutathione S-transferase and metabolism behavior of chlorambucil. Pharmacol Res. 2003 Dec;48(6):623-30. [PubMed:14527828 ]

Showing metabocard for Chlorambucil (HMDB0014436)

MOL for HMDB0014436 (Chlorambucil)

3D MOL for HMDB0014436 (Chlorambucil)

3D SDF for HMDB0014436 (Chlorambucil)

3D-SDF for HMDB0014436 (Chlorambucil)

PDB for HMDB0014436 (Chlorambucil)

3D PDB for HMDB0014436 (Chlorambucil)

SMILES for HMDB0014436 (Chlorambucil)

INCHI for HMDB0014436 (Chlorambucil)

Structure for HMDB0014436 (Chlorambucil)

3D Structure for HMDB0014436 (Chlorambucil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References