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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015176

Secondary Accession Numbers

HMDB15176

Metabolite Identification

Common Name

Melphalan

Description

Melphalan, also known as L-sarcolysine 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. Melphalan is a drug which is used for the palliative treatment of multiple myeloma and for the palliation of non-resectable epithelial carcinoma of the ovary. has also been used alone or as part of various chemotherapeutic regimens as an adjunct to surgery in the treatment of breast cancer, alone or in combination regimens for palliative treatment of locally recurrent or unresectable in-transit metastatic melanoma of the extremities, as well as for the treatment of amyloidosis with prednisone. Melphalan is a very strong basic compound (based on its pKa). Melphalan is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.

Structure

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

HMDB0015176
     RDKit          3D
Melphalan
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.1291   -0.6145   -0.6885 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399   -0.1278   -0.7349 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9564   -1.1164    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -0.7348    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291    0.0704    1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929    0.4120    1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -0.0300    0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5577    0.3664    0.3170 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    1.7645    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871    1.9246   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9974    3.6720   -1.3690 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6041   -0.5448    0.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.0136    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831   -2.3267    1.6505 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -0.8094   -0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239   -1.1530   -0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    1.2437   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5839    1.8647   -0.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8084    1.8269    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1497   -1.6727   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5530   -0.3091    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032   -0.1519   -1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983   -1.1647    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343   -2.1194   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263    0.3948    1.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6796    1.0393    1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    2.3675   -0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171    2.1704    0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769    1.5352   -1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6158    1.3436   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8148   -0.3667    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -0.3617    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0059   -2.6587    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0091   -2.3667   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -1.1770   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636   -1.7793   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1741    1.6028    1.2402 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  6
  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


  Mrv0541 04191212162D          

 19 19  0  0  1  0            999 V2000
   12.3674  -12.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6542  -12.9393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0805  -12.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3674  -11.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6542  -13.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9376  -12.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7972  -12.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0805  -11.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7937  -11.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5069  -11.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2200  -11.7118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9366  -11.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2200  -12.5347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6463  -11.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9366  -10.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9357  -11.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2137  -11.3068    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.3791  -14.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3793  -15.0110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 15  2  0  0  0  0
  8  9  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015176

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](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)/t12-/m0/s1

> <INCHI_KEY>
SGDBTWWWUNNDEQ-LBPRGKRZSA-N

> <FORMULA>
C13H18Cl2N2O2

> <MOLECULAR_WEIGHT>
305.2

> <EXACT_MASS>
304.074533244

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.383697992820657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-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>
melphalan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015176
     RDKit          3D
Melphalan
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.1291   -0.6145   -0.6885 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399   -0.1278   -0.7349 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9564   -1.1164    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -0.7348    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291    0.0704    1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929    0.4120    1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -0.0300    0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5577    0.3664    0.3170 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    1.7645    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871    1.9246   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9974    3.6720   -1.3690 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6041   -0.5448    0.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.0136    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831   -2.3267    1.6505 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -0.8094   -0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239   -1.1530   -0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    1.2437   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5839    1.8647   -0.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8084    1.8269    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1497   -1.6727   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5530   -0.3091    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032   -0.1519   -1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983   -1.1647    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343   -2.1194   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263    0.3948    1.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6796    1.0393    1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    2.3675   -0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171    2.1704    0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769    1.5352   -1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6158    1.3436   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8148   -0.3667    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -0.3617    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0059   -2.6587    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0091   -2.3667   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -1.1770   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636   -1.7793   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1741    1.6028    1.2402 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  6
  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                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      23.086 -23.392   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      21.755 -24.153   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      24.417 -24.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.086 -21.849   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.755 -25.696   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.417 -23.392   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.755 -23.392   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.417 -21.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.748 -21.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.080 -21.088   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.411 -21.862   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.748 -21.088   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      28.411 -23.398   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      31.073 -21.862   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      29.748 -19.545   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      20.413 -21.880   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      19.066 -21.106   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      23.108 -26.477   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      23.108 -28.021   0.000  0.00  0.00          Cl+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2   18                                                       
CONECT    6    2   16                                                       
CONECT    7    3    9                                                       
CONECT    8    4    9                                                       
CONECT    9    7   10    8                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14   15                                                  
CONECT   13   11                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    6   17                                                       
CONECT   17   16                                                            
CONECT   18    5   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0015176
HETATM    1  N1  UNL     1       5.129  -0.614  -0.689  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.740  -0.128  -0.735  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.956  -1.116   0.075  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.516  -0.735   0.113  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.029   0.070   1.148  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.293   0.412   1.181  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.194  -0.030   0.191  1.00  0.00           C  
HETATM    8  N2  UNL     1      -2.558   0.366   0.317  1.00  0.00           N  
HETATM    9  C7  UNL     1      -2.851   1.764   0.112  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.687   1.925  -1.155  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -3.997   3.672  -1.369  1.00  0.00          CL  
HETATM   12  C9  UNL     1      -3.604  -0.545   0.669  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.168  -2.014   0.591  1.00  0.00           C  
HETATM   14 CL2  UNL     1      -1.783  -2.327   1.650  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -0.732  -0.809  -0.813  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.624  -1.153  -0.838  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.648   1.244  -0.200  1.00  0.00           C  
HETATM   18  O1  UNL     1       2.584   1.865  -0.207  1.00  0.00           O  
HETATM   19  O2  UNL     1       4.808   1.827   0.316  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.150  -1.673  -0.647  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.553  -0.309   0.225  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.403  -0.152  -1.783  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.298  -1.165   1.136  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.034  -2.119  -0.398  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.726   0.395   1.900  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.680   1.039   1.977  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.932   2.367  -0.059  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.417   2.170   0.975  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.077   1.535  -1.992  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.616   1.344  -1.006  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.815  -0.367   1.769  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.542  -0.362   0.135  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.006  -2.659   0.988  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.009  -2.367  -0.430  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.375  -1.177  -1.614  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.964  -1.779  -1.660  1.00  0.00           H  
HETATM   37  H18 UNL     1       5.174   1.603   1.240  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

HMDB0015176
     RDKit          3D
Melphalan
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.1291   -0.6145   -0.6885 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399   -0.1278   -0.7349 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9564   -1.1164    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -0.7348    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291    0.0704    1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929    0.4120    1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -0.0300    0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5577    0.3664    0.3170 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    1.7645    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871    1.9246   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9974    3.6720   -1.3690 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6041   -0.5448    0.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.0136    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831   -2.3267    1.6505 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -0.8094   -0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239   -1.1530   -0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    1.2437   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5839    1.8647   -0.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8084    1.8269    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1497   -1.6727   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5530   -0.3091    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032   -0.1519   -1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983   -1.1647    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343   -2.1194   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263    0.3948    1.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6796    1.0393    1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    2.3675   -0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171    2.1704    0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769    1.5352   -1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6158    1.3436   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8148   -0.3667    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -0.3617    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0059   -2.6587    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0091   -2.3667   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -1.1770   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636   -1.7793   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1741    1.6028    1.2402 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  6
  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
3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine	ChEBI
3-p-(Di(2-chloroethyl)amino)-phenyl-L-alanine	ChEBI
4-(Bis(2-chloroethyl)amino)-L-phenylalanine	ChEBI
L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine	ChEBI
L-PAM	ChEBI
L-Phenylalanine mustard	ChEBI
L-Sarcolysine	ChEBI
Melfalano	ChEBI
Melphalanum	ChEBI
p-Bis(beta-chloroethyl)aminophenylalanine	ChEBI
p-Di-(2-chloroethyl)amino-L-phenylalanine	ChEBI
p-L-Sarcolysin	ChEBI
p-N,N-Bis(2-chloroethyl)amino-L-phenylalanine	ChEBI
p-N-Bis(2-chloroethyl)amino-L-phenylalanine	ChEBI
Phenylalanine mustard	ChEBI
Phenylalanine nitrogen mustard	ChEBI
Alkeran	Kegg
p-Bis(b-chloroethyl)aminophenylalanine	Generator
p-Bis(β-chloroethyl)aminophenylalanine	Generator
4-(Bis(2-chloroethyl)amino)phenylalanine	HMDB
Medphalan	HMDB
Merphalan	HMDB
Sarcolysine	HMDB
Sarkolysin	HMDB
Mustard, phenylalanine	HMDB

Chemical Formula

C₁₃H₁₈Cl₂N₂O₂

Average Molecular Weight

305.2

Monoisotopic Molecular Weight

304.074533244

IUPAC Name

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

Traditional Name

melphalan

CAS Registry Number

148-82-3

SMILES

N[C@@H](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)/t12-/m0/s1

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:28876 )
non-proteinogenic L-alpha-amino acid (CHEBI:28876 )
L-phenylalanine derivative (CHEBI:28876 )
nitrogen mustard (CHEBI:28876 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0015176)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.36 g/L	Not Available
LogP	0.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	168.69	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001269

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
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	31.38 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]+	168.784	30932474
DeepCCS	[M-H]-	166.426	30932474
DeepCCS	[M-2H]-	199.313	30932474
DeepCCS	[M+Na]+	174.877	30932474
AllCCS	[M+H]+	165.3	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	168.1	32859911
AllCCS	[M+Na]+	168.9	32859911
AllCCS	[M-H]-	167.5	32859911
AllCCS	[M+Na-2H]-	168.0	32859911
AllCCS	[M+HCOO]-	168.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	3.73 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1917 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.44 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	96.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1267.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	286.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	74.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	402.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	381.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	941.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	361.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1182.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	253.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	360.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	277.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melphalan	N[C@@H](CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O	3478.3	Standard polar	33892256
Melphalan	N[C@@H](CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O	2494.8	Standard non polar	33892256
Melphalan	N[C@@H](CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O	2603.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melphalan,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1	2498.1	Semi standard non polar	33892256
Melphalan,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O	2637.9	Semi standard non polar	33892256
Melphalan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C	2533.9	Semi standard non polar	33892256
Melphalan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C	2469.6	Standard non polar	33892256
Melphalan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C	2993.4	Standard polar	33892256
Melphalan,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C	2714.3	Semi standard non polar	33892256
Melphalan,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C	2617.7	Standard non polar	33892256
Melphalan,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C	3167.8	Standard polar	33892256
Melphalan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2666.2	Semi standard non polar	33892256
Melphalan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2600.7	Standard non polar	33892256
Melphalan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2828.3	Standard polar	33892256
Melphalan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1	2759.9	Semi standard non polar	33892256
Melphalan,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O	2867.9	Semi standard non polar	33892256
Melphalan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3009.2	Semi standard non polar	33892256
Melphalan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2975.5	Standard non polar	33892256
Melphalan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3139.1	Standard polar	33892256
Melphalan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3165.9	Semi standard non polar	33892256
Melphalan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3047.1	Standard non polar	33892256
Melphalan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3210.6	Standard polar	33892256
Melphalan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3332.2	Semi standard non polar	33892256
Melphalan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3230.5	Standard non polar	33892256
Melphalan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(N(CCCl)CCCl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3044.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Melphalan GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-3890000000-153ff87813e7a797c73b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melphalan GC-MS (1 TMS) - 70eV, Positive	splash10-01c3-8295000000-421b0e52574345db725f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melphalan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melphalan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melphalan LC-ESI-qTof , Positive-QTOF	splash10-000w-2930000000-b95beb5e9c3e61b7687f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melphalan , positive-QTOF	splash10-000w-2930000000-b95beb5e9c3e61b7687f	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 10V, Positive-QTOF	splash10-0a4i-0093000000-78045bae5e6c1e79e22d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 20V, Positive-QTOF	splash10-0a4i-1490000000-3b1f7009692b1139989b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 40V, Positive-QTOF	splash10-02t9-3930000000-b0f45ffda87388d4384a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 10V, Negative-QTOF	splash10-0udi-0049000000-8c401366ace5d7fc1f08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 20V, Negative-QTOF	splash10-0v4i-1192000000-fd136d877921c8afed95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 40V, Negative-QTOF	splash10-00di-9530000000-511158435cb1ef063085	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 10V, Positive-QTOF	splash10-0a4i-0095000000-3f3242a1d9debe0c8315	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 20V, Positive-QTOF	splash10-00bi-0090000000-91067233804f48cd760a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 40V, Positive-QTOF	splash10-014j-0930000000-af3e37be6b85ec7f144b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 10V, Negative-QTOF	splash10-001i-7090000000-6793f4f7ed0a2c22f972	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melphalan 40V, Negative-QTOF	splash10-001i-9000000000-ed9c052b92676bc8a30b	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01042	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01042	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

DB01042

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

405297

KEGG Compound ID

C07122

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Melphalan

METLIN ID

Not Available

PubChem Compound

460612

PDB ID

Not Available

ChEBI ID

28876

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

Moscow JA, Swanson CA, Cowan KH: Decreased melphalan accumulation in a human breast cancer cell line selected for resistance to melphalan. Br J Cancer. 1993 Oct;68(4):732-7. [PubMed:8398701 ]
Souliotis VL, Dimopoulos MA, Episkopou HG, Kyrtopoulos SA, Sfikakis PP: Preferential in vivo DNA repair of melphalan-induced damage in human genes is greatly affected by the local chromatin structure. DNA Repair (Amst). 2006 Aug 13;5(8):972-85. Epub 2006 Jun 15. [PubMed:16781199 ]
Loeber R, Michaelson E, Fang Q, Campbell C, Pegg AE, Tretyakova N: Cross-linking of the DNA repair protein Omicron6-alkylguanine DNA alkyltransferase to DNA in the presence of antitumor nitrogen mustards. Chem Res Toxicol. 2008 Apr;21(4):787-95. doi: 10.1021/tx7004508. Epub 2008 Feb 14. [PubMed:18324787 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Shnitsar V, Eckardt R, Gupta S, Grottker J, Muller GA, Koepsell H, Burckhardt G, Hagos Y: Expression of human organic cation transporter 3 in kidney carcinoma cell lines increases chemosensitivity to melphalan, irinotecan, and vincristine. Cancer Res. 2009 Feb 15;69(4):1494-501. doi: 10.1158/0008-5472.CAN-08-2483. Epub 2009 Feb 3. [PubMed:19190342 ]

Showing metabocard for Melphalan (HMDB0015176)

MOL for HMDB0015176 (Melphalan)

3D MOL for HMDB0015176 (Melphalan)

3D SDF for HMDB0015176 (Melphalan)

3D-SDF for HMDB0015176 (Melphalan)

PDB for HMDB0015176 (Melphalan)

3D PDB for HMDB0015176 (Melphalan)

SMILES for HMDB0015176 (Melphalan)

INCHI for HMDB0015176 (Melphalan)

Structure for HMDB0015176 (Melphalan)

3D Structure for HMDB0015176 (Melphalan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Transporters

References