Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:41:12 UTC

Update Date

2021-09-26 22:52:20 UTC

HMDB ID

HMDB0244533

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Medphalan

Description

Medphalan, also known as sarcolysin or L-PAM, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on Medphalan. This compound has been identified in human blood as reported by (PMID: 31557052 ). Medphalan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Medphalan 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

HMDB0244533
     RDKit          3D
Medphalan
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.4101    0.4423    0.0391 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445    0.5435   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854   -0.6187    0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.5302    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761   -1.1359   -0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -1.0496   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -0.3587    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -0.2380   -0.0085 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541   -0.0519    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0805   -1.1800    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2731   -1.5530    0.2558 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -0.2694   -1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050    1.0967   -1.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749    2.3511   -1.6780 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2662    0.2442    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187    0.1701    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5928    0.7227   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178    0.6912   -2.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095    0.9271   -2.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7734    1.4021   -0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    0.0911    0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6786    1.5058    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6878   -1.5637    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -0.5811    1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7050   -1.6909   -1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -1.5446   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792    0.8867    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532    0.1217    2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4703   -2.0670    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -0.8610    2.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050   -0.3970   -2.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -1.0934   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9215    1.0350   -2.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3340    1.2780   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800    0.8025    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    0.6294    2.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869    1.8429   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
 16  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
M  END


  Mrv1572004201615532D          

 19 19  0  0  0  0            999 V2000
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  9  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  2  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244533

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)

> <INCHI_KEY>
SGDBTWWWUNNDEQ-UHFFFAOYSA-N

> <FORMULA>
C13H18Cl2N2O2

> <MOLECULAR_WEIGHT>
305.2

> <EXACT_MASS>
304.0745332

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.449679943615696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.22

> <JCHEM_LOGP>
0.25219622473316816

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2884430296765705

> <JCHEM_PKA_STRONGEST_BASIC>
9.512487752295659

> <JCHEM_POLAR_SURFACE_AREA>
66.56

> <JCHEM_REFRACTIVITY>
78.2315

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alkeran

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244533
     RDKit          3D
Medphalan
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.4101    0.4423    0.0391 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445    0.5435   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854   -0.6187    0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.5302    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761   -1.1359   -0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -1.0496   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -0.3587    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -0.2380   -0.0085 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541   -0.0519    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0805   -1.1800    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2731   -1.5530    0.2558 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -0.2694   -1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050    1.0967   -1.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749    2.3511   -1.6780 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2662    0.2442    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187    0.1701    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5928    0.7227   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178    0.6912   -2.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095    0.9271   -2.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7734    1.4021   -0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    0.0911    0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6786    1.5058    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6878   -1.5637    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -0.5811    1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7050   -1.6909   -1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -1.5446   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792    0.8867    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532    0.1217    2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4703   -2.0670    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -0.8610    2.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050   -0.3970   -2.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -1.0934   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9215    1.0350   -2.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3340    1.2780   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800    0.8025    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    0.6294    2.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869    1.8429   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
 16  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 20-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-16         0                                  
HETATM    1  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       5.335   0.000   0.000  0.00  0.00          Cl+0
HETATM   15 Cl   UNK     0      10.669   0.000   0.000  0.00  0.00          Cl+0
HETATM   16  N   UNK     0      10.669  -9.240   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       8.002  -3.080   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
CONECT    1    3   10                                                       
CONECT    2    4   10                                                       
CONECT    3    1   11                                                       
CONECT    4    2   11                                                       
CONECT    5    7   14                                                       
CONECT    6    8   15                                                       
CONECT    7    5   17                                                       
CONECT    8    6   17                                                       
CONECT    9   10   12                                                       
CONECT   10    1    2    9                                                  
CONECT   11    3    4   17                                                  
CONECT   12    9   13   16                                                  
CONECT   13   12   18   19                                                  
CONECT   14    5                                                            
CONECT   15    6                                                            
CONECT   16   12                                                            
CONECT   17    7    8   11                                                  
CONECT   18   13                                                            
CONECT   19   13                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0244533
HETATM    1  N1  UNL     1       5.410   0.442   0.039  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.944   0.543  -0.113  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.285  -0.619   0.558  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.826  -0.530   0.416  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.176  -1.136  -0.647  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.207  -1.050  -0.778  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.905  -0.359   0.157  1.00  0.00           C  
HETATM    8  N2  UNL     1      -2.332  -0.238  -0.008  1.00  0.00           N  
HETATM    9  C7  UNL     1      -3.154  -0.052   1.157  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.081  -1.180   1.479  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -5.273  -1.553   0.256  1.00  0.00          CL  
HETATM   12  C9  UNL     1      -2.912  -0.269  -1.322  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.505   1.097  -1.692  1.00  0.00           C  
HETATM   14 CL2  UNL     1      -2.275   2.351  -1.678  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -0.266   0.244   1.212  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.119   0.170   1.364  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.593   0.723  -1.532  1.00  0.00           C  
HETATM   18  O1  UNL     1       4.518   0.691  -2.387  1.00  0.00           O  
HETATM   19  O2  UNL     1       2.309   0.927  -2.010  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.773   1.402  -0.156  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.642   0.091   0.989  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.679   1.506   0.404  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.688  -1.564   0.144  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.571  -0.581   1.634  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.705  -1.691  -1.405  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.684  -1.545  -1.606  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.779   0.887   1.069  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.553   0.122   2.071  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.470  -2.067   1.760  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.640  -0.861   2.405  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.105  -0.397  -2.103  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.605  -1.093  -1.507  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.921   1.035  -2.717  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.334   1.278  -1.007  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.780   0.803   1.956  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.656   0.629   2.179  1.00  0.00           H  
HETATM   37  H18 UNL     1       1.887   1.843  -1.817  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3   17   22
CONECT    3    4   23   24
CONECT    4    5    5   16
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8   15
CONECT    8    9   12
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   15   16   16   35
CONECT   16   36
CONECT   17   18   18   19
CONECT   19   37
END

HMDB0244533
     RDKit          3D
Medphalan
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.4101    0.4423    0.0391 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445    0.5435   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854   -0.6187    0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.5302    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761   -1.1359   -0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -1.0496   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -0.3587    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -0.2380   -0.0085 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541   -0.0519    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0805   -1.1800    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2731   -1.5530    0.2558 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -0.2694   -1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050    1.0967   -1.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749    2.3511   -1.6780 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2662    0.2442    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187    0.1701    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5928    0.7227   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178    0.6912   -2.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095    0.9271   -2.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7734    1.4021   -0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    0.0911    0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6786    1.5058    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6878   -1.5637    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -0.5811    1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7050   -1.6909   -1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -1.5446   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7792    0.8867    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532    0.1217    2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4703   -2.0670    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -0.8610    2.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050   -0.3970   -2.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -1.0934   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9215    1.0350   -2.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3340    1.2780   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800    0.8025    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    0.6294    2.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869    1.8429   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
 16  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Sarcolysin	Kegg
2-Amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoate	HMDB
2-Amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoate	HMDB
L-PAM	HMDB
Mustard, phenylalanine	HMDB
Phenylalanine mustard	HMDB
Alkeran	HMDB
Melphalan	HMDB
Sarcolysine	HMDB
Merphalan	HMDB
4-(Bis(2-chloroethyl)amino)phenylalanine	HMDB
Sarkolysin	HMDB
Medphalan	MeSH

Chemical Formula

C₁₃H₁₈Cl₂N₂O₂

Average Molecular Weight

305.2

Monoisotopic Molecular Weight

304.0745332

IUPAC Name

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

Traditional Name

alkeran

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)

InChI Key

SGDBTWWWUNNDEQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
Aniline or substituted anilines
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Nitrogen mustard
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Tertiary amine
Carboxylic acid
Monocarboxylic acid or derivatives
Alkyl chloride
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Primary amine
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:82339 )

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	-0.22	ALOGPS
logP	0.25	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	1.29	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.56 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	78.23 m³·mol⁻¹	ChemAxon
Polarizability	31.45 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]+	166.404	30932474
DeepCCS	[M-H]-	164.046	30932474
DeepCCS	[M-2H]-	197.429	30932474
DeepCCS	[M+Na]+	172.597	30932474
AllCCS	[M+H]+	165.3	32859911
AllCCS	[M+H-H2O]+	162.3	32859911
AllCCS	[M+NH4]+	168.2	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	167.5	32859911
AllCCS	[M+Na-2H]-	168.0	32859911
AllCCS	[M+HCOO]-	168.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Medphalan	NC(CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O	3501.8	Standard polar	33892256
Medphalan	NC(CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O	2491.5	Standard non polar	33892256
Medphalan	NC(CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O	2594.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Medphalan,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C	2531.3	Semi standard non polar	33892256
Medphalan,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C	2485.4	Standard non polar	33892256
Medphalan,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C	2980.0	Standard polar	33892256
Medphalan,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C	2705.7	Semi standard non polar	33892256
Medphalan,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C	2634.6	Standard non polar	33892256
Medphalan,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C	3168.9	Standard polar	33892256
Medphalan,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2661.8	Semi standard non polar	33892256
Medphalan,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2610.8	Standard non polar	33892256
Medphalan,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2841.8	Standard polar	33892256
Medphalan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2971.5	Semi standard non polar	33892256
Medphalan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2978.5	Standard non polar	33892256
Medphalan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3134.3	Standard polar	33892256
Medphalan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3119.0	Semi standard non polar	33892256
Medphalan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3044.1	Standard non polar	33892256
Medphalan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3222.1	Standard polar	33892256
Medphalan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3307.1	Semi standard non polar	33892256
Medphalan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3237.1	Standard non polar	33892256
Medphalan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3050.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Medphalan GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-3890000000-153ff87813e7a797c73b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medphalan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medphalan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medphalan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medphalan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medphalan GC-MS (TBDMS_1_2) - 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 - Medphalan 10V, Positive-QTOF	splash10-0a4i-0093000000-78045bae5e6c1e79e22d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 20V, Positive-QTOF	splash10-0a4i-1490000000-3b1f7009692b1139989b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 40V, Positive-QTOF	splash10-02t9-3930000000-b0f45ffda87388d4384a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 10V, Negative-QTOF	splash10-0udi-0049000000-8c401366ace5d7fc1f08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 20V, Negative-QTOF	splash10-0v4i-1192000000-fd136d877921c8afed95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 40V, Negative-QTOF	splash10-00di-9530000000-511158435cb1ef063085	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 10V, Positive-QTOF	splash10-0a4i-0095000000-3f3242a1d9debe0c8315	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 20V, Positive-QTOF	splash10-00bi-0090000000-91067233804f48cd760a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 40V, Positive-QTOF	splash10-014j-0930000000-af3e37be6b85ec7f144b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 10V, Negative-QTOF	splash10-001i-7090000000-6793f4f7ed0a2c22f972	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medphalan 40V, Negative-QTOF	splash10-001i-9000000000-ed9c052b92676bc8a30b	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

3913

KEGG Compound ID

C19256

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4053

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 Medphalan (HMDB0244533)

MOL for HMDB0244533 (Medphalan)

3D MOL for HMDB0244533 (Medphalan)

3D SDF for HMDB0244533 (Medphalan)

3D-SDF for HMDB0244533 (Medphalan)

PDB for HMDB0244533 (Medphalan)

3D PDB for HMDB0244533 (Medphalan)

SMILES for HMDB0244533 (Medphalan)

INCHI for HMDB0244533 (Medphalan)

Structure for HMDB0244533 (Medphalan)

3D Structure for HMDB0244533 (Medphalan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra