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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:03:43 UTC

Update Date

2021-09-26 22:54:50 UTC

HMDB ID

HMDB0246018

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,4-Dehydrochlorambucil

Description

3,4-Dehydrochlorambucil belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Based on a literature review very few articles have been published on 3,4-Dehydrochlorambucil. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,4-dehydrochlorambucil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,4-Dehydrochlorambucil is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0246018
     RDKit          3D
3,4-Dehydrochlorambucil
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.3250    0.8892    1.5969 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9515    0.2145    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3288    0.3724    0.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018   -0.6914   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222   -0.6692    0.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -0.3311   -0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -0.3068   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557   -0.5985    0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -0.5665    0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -0.2335   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -0.2430    0.0690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8592    0.3058   -0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7054    0.8246   -2.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547    1.4413   -2.5798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762   -0.9338    1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5578   -0.0130    2.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    0.9808    2.1791 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    0.0558   -1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663    0.0285   -1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6892    0.8353   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6055   -1.7169   -0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479   -0.4543   -1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4426   -0.9532    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -0.0631   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124   -0.8654    1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -0.7938    1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7672   -0.3949   -0.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    1.1763   -0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975    1.7434   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4995    0.0620   -2.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -1.5401    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782   -1.7415    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7301   -0.5893    3.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7280    0.6905    2.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    0.3134   -2.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    0.2705   -2.5591 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  2  3
  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
  6 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
M  END


  Mrv1652309112101032D          

 19 19  0  0  0  0            999 V2000
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246018

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC=CC1=CC=C(C=C1)N(CCCl)CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C14H17Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h1-2,4-7H,3,8-11H2,(H,18,19)

> <INCHI_KEY>
PXOQTPQOIMSYSF-UHFFFAOYSA-N

> <FORMULA>
C14H17Cl2NO2

> <MOLECULAR_WEIGHT>
302.2

> <EXACT_MASS>
301.0636342

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.586653266069025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{4-[bis(2-chloroethyl)amino]phenyl}but-3-enoic acid

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
3.6579333253333335

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.300708767305182

> <JCHEM_PKA_STRONGEST_BASIC>
1.665300028863486

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
80.7994

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{4-[bis(2-chloroethyl)amino]phenyl}but-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246018
     RDKit          3D
3,4-Dehydrochlorambucil
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.3250    0.8892    1.5969 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9515    0.2145    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3288    0.3724    0.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018   -0.6914   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222   -0.6692    0.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -0.3311   -0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -0.3068   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557   -0.5985    0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -0.5665    0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -0.2335   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -0.2430    0.0690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8592    0.3058   -0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7054    0.8246   -2.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547    1.4413   -2.5798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762   -0.9338    1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5578   -0.0130    2.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    0.9808    2.1791 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    0.0558   -1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663    0.0285   -1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6892    0.8353   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6055   -1.7169   -0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479   -0.4543   -1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4426   -0.9532    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -0.0631   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124   -0.8654    1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -0.7938    1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7672   -0.3949   -0.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    1.1763   -0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975    1.7434   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4995    0.0620   -2.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -1.5401    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782   -1.7415    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7301   -0.5893    3.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7280    0.6905    2.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    0.3134   -2.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    0.2705   -2.5591 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  2  3
  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
  6 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335 -10.780   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -6.668  -8.470   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -2.667   0.000   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -5.335   3.080   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       0.000   3.080   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    3   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0246018
HETATM    1  O1  UNL     1       5.325   0.889   1.597  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.951   0.214   0.723  1.00  0.00           C  
HETATM    3  O2  UNL     1       7.329   0.372   0.648  1.00  0.00           O  
HETATM    4  C2  UNL     1       5.202  -0.691  -0.157  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.722  -0.669   0.120  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.868  -0.331  -0.811  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.437  -0.307  -0.552  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.856  -0.598   0.644  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.501  -0.566   0.827  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.417  -0.234  -0.192  1.00  0.00           C  
HETATM   11  N1  UNL     1      -2.802  -0.243   0.069  1.00  0.00           N  
HETATM   12  C9  UNL     1      -3.859   0.306  -0.658  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.705   0.825  -2.045  1.00  0.00           C  
HETATM   14 CL1  UNL     1      -5.355   1.441  -2.580  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -3.176  -0.934   1.329  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.558  -0.013   2.411  1.00  0.00           C  
HETATM   17 CL2  UNL     1      -4.985   0.981   2.179  1.00  0.00          CL  
HETATM   18  C13 UNL     1      -0.800   0.056  -1.389  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.566   0.028  -1.588  1.00  0.00           C  
HETATM   20  H1  UNL     1       7.689   0.835  -0.195  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.605  -1.717  -0.037  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.348  -0.454  -1.254  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.443  -0.953   1.122  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.239  -0.063  -1.790  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.512  -0.865   1.483  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.860  -0.794   1.807  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.767  -0.395  -0.714  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.272   1.176  -0.010  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.098   1.743  -2.071  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.499   0.062  -2.799  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.126  -1.540   1.043  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.478  -1.741   1.574  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.730  -0.589   3.378  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.728   0.690   2.701  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.383   0.313  -2.255  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.008   0.270  -2.559  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6    6   23
CONECT    6    7   24
CONECT    7    8    8   19
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   18
CONECT   11   12   15
CONECT   12   13   27   28
CONECT   13   14   29   30
CONECT   15   16   31   32
CONECT   16   17   33   34
CONECT   18   19   19   35
CONECT   19   36
END

HMDB0246018
     RDKit          3D
3,4-Dehydrochlorambucil
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.3250    0.8892    1.5969 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9515    0.2145    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3288    0.3724    0.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018   -0.6914   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222   -0.6692    0.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -0.3311   -0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -0.3068   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557   -0.5985    0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -0.5665    0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -0.2335   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -0.2430    0.0690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8592    0.3058   -0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7054    0.8246   -2.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547    1.4413   -2.5798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762   -0.9338    1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5578   -0.0130    2.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    0.9808    2.1791 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    0.0558   -1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663    0.0285   -1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6892    0.8353   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6055   -1.7169   -0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479   -0.4543   -1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4426   -0.9532    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -0.0631   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124   -0.8654    1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -0.7938    1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7672   -0.3949   -0.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    1.1763   -0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975    1.7434   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4995    0.0620   -2.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -1.5401    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782   -1.7415    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7301   -0.5893    3.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7280    0.6905    2.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    0.3134   -2.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    0.2705   -2.5591 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  2  3
  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
  6 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₇Cl₂NO₂

Average Molecular Weight

302.2

Monoisotopic Molecular Weight

301.0636342

IUPAC Name

4-{4-[bis(2-chloroethyl)amino]phenyl}but-3-enoic acid

Traditional Name

4-{4-[bis(2-chloroethyl)amino]phenyl}but-3-enoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC=CC1=CC=C(C=C1)N(CCCl)CCCl

InChI Identifier

InChI=1S/C14H17Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h1-2,4-7H,3,8-11H2,(H,18,19)

InChI Key

PXOQTPQOIMSYSF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.27	ALOGPS
logP	3.66	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	1.67	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	8	ChemAxon
Refractivity	80.8 m³·mol⁻¹	ChemAxon
Polarizability	31.59 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]+	166.006	30932474
DeepCCS	[M-H]-	163.611	30932474
DeepCCS	[M-2H]-	196.495	30932474
DeepCCS	[M+Na]+	172.021	30932474
AllCCS	[M+H]+	162.7	32859911
AllCCS	[M+H-H2O]+	159.8	32859911
AllCCS	[M+NH4]+	165.5	32859911
AllCCS	[M+Na]+	166.3	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	165.2	32859911
AllCCS	[M+HCOO]-	165.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dehydrochlorambucil	OC(=O)CC=CC1=CC=C(C=C1)N(CCCl)CCCl	3624.0	Standard polar	33892256
3,4-Dehydrochlorambucil	OC(=O)CC=CC1=CC=C(C=C1)N(CCCl)CCCl	2510.7	Standard non polar	33892256
3,4-Dehydrochlorambucil	OC(=O)CC=CC1=CC=C(C=C1)N(CCCl)CCCl	2610.2	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 - 3,4-Dehydrochlorambucil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-0590000000-2d244a1a21d3456db718	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dehydrochlorambucil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dehydrochlorambucil GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dehydrochlorambucil GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - 3,4-Dehydrochlorambucil 10V, Positive-QTOF	splash10-0ue9-0079000000-ecb8e8999edeb32c7ea2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dehydrochlorambucil 20V, Positive-QTOF	splash10-0ff0-0092000000-39f9427bfdf8bc34dfc7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dehydrochlorambucil 40V, Positive-QTOF	splash10-0006-1930000000-1911413f08ba97dd1380	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dehydrochlorambucil 10V, Negative-QTOF	splash10-001i-9014000000-b9a51fe143b0fc9d750a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dehydrochlorambucil 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dehydrochlorambucil 40V, Negative-QTOF	splash10-001i-9000000000-68a342ef73b428b5a9d3	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28716640

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

175397

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 3,4-Dehydrochlorambucil (HMDB0246018)

MOL for HMDB0246018 (3,4-Dehydrochlorambucil)

3D MOL for HMDB0246018 (3,4-Dehydrochlorambucil)

3D SDF for HMDB0246018 (3,4-Dehydrochlorambucil)

3D-SDF for HMDB0246018 (3,4-Dehydrochlorambucil)

PDB for HMDB0246018 (3,4-Dehydrochlorambucil)

3D PDB for HMDB0246018 (3,4-Dehydrochlorambucil)

SMILES for HMDB0246018 (3,4-Dehydrochlorambucil)

INCHI for HMDB0246018 (3,4-Dehydrochlorambucil)

Structure for HMDB0246018 (3,4-Dehydrochlorambucil)

3D Structure for HMDB0246018 (3,4-Dehydrochlorambucil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra