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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015385

Secondary Accession Numbers

HMDB15385

Metabolite Identification

Common Name

Lisdexamfetamine

Description

Lisdexamfetamine (L-lysine-d-amphetamine) is a prodrug of the psychostimulant d-amphetamine coupled with the essential amino acid L-lysine. It was developed so that the amphetamine psychostimulant is released and activated more slowly as the prodrug molecule is hydrolyzed consequently cleaving off the amino acid-during the first pass through the intestines and/or the liver. Amphetamines target the trace amine-associated receptor 1 (TAAR1). Amphetamine is also believed to exert its effects by binding to the monoamine transporters (the dopamine transporter or DAT) and increasing extracellular levels of the biogenic amines dopamine, norepinephrine (noradrenaline) and serotonin.

Structure

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

HMDB0015385
     RDKit          3D
Lisdexamfetamine
 44 44  0  0  0  0  0  0  0  0999 V2000
    1.5914   -0.4858    1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -0.1235   -0.1799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7052   -0.3424   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7252    0.5386   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9213    1.8280   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    2.6877   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033    2.2024    0.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4203    0.9157    1.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854    0.0742    0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3153   -0.8815   -0.7629 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8408   -0.2398   -1.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    1.0111   -1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.0359   -1.8511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5923   -2.4252   -1.7993 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2659   -0.7461   -1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246   -1.0898    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3821   -0.8490    1.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411    0.5703    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255    1.4466    1.5977 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -1.4985    1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233    0.2936    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5908   -0.5078    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329    0.9456   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -1.3902   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354   -0.1759   -1.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    2.1571   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    3.6900   -0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3220    2.8826    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285    0.5744    2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.9481    1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762   -1.9400   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0513   -0.6757   -2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482   -3.0289   -1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -2.7834   -2.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0322   -1.3079   -1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519    0.3300   -1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394   -2.1515    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -0.4767    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2022   -1.4985    0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972   -1.1277    2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1680    0.9070    0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353    0.6491    1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    2.1547    2.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2313    1.8714    0.8668 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  2  0
  2 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  9  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  6
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

1255
  Mrv0541 02231215212D          

 19 19  0  0  0  0            999 V2000
   -0.8608   -0.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2907    0.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768    0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8618    0.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478    0.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    0.2319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2811    0.6453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961    0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101    0.6470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4250    0.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1390    0.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8540    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5679    0.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681   -0.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -0.5914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7091    1.4720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2829    0.2387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  1  0  0  0
 10 17  2  0  0  0  0
 11 18  1  1  0  0  0
 15 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015385

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C15H25N3O/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19)/t12-,14-/m0/s1

> <INCHI_KEY>
VOBHXZCDAVEXEY-JSGCOSHPSA-N

> <FORMULA>
C15H25N3O

> <MOLECULAR_WEIGHT>
263.3785

> <EXACT_MASS>
263.199762437

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.28096264112009

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.135830796

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.885676132636696

> <JCHEM_PKA_STRONGEST_BASIC>
10.21284535333755

> <JCHEM_POLAR_SURFACE_AREA>
81.14

> <JCHEM_REFRACTIVITY>
78.3148

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vyvanse

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015385
     RDKit          3D
Lisdexamfetamine
 44 44  0  0  0  0  0  0  0  0999 V2000
    1.5914   -0.4858    1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -0.1235   -0.1799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7052   -0.3424   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7252    0.5386   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9213    1.8280   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    2.6877   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033    2.2024    0.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4203    0.9157    1.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854    0.0742    0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3153   -0.8815   -0.7629 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8408   -0.2398   -1.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    1.0111   -1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.0359   -1.8511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5923   -2.4252   -1.7993 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2659   -0.7461   -1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246   -1.0898    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3821   -0.8490    1.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411    0.5703    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255    1.4466    1.5977 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -1.4985    1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233    0.2936    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5908   -0.5078    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329    0.9456   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -1.3902   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354   -0.1759   -1.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    2.1571   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    3.6900   -0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3220    2.8826    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285    0.5744    2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.9481    1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762   -1.9400   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0513   -0.6757   -2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482   -3.0289   -1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -2.7834   -2.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0322   -1.3079   -1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519    0.3300   -1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394   -2.1515    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -0.4767    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2022   -1.4985    0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972   -1.1277    2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1680    0.9070    0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353    0.6491    1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    2.1547    2.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2313    1.8714    0.8668 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  2  0
  2 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  9  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  6
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1255                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.607  -1.110   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.940  -1.882   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.274  -1.113   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.276   0.427   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.943   1.198   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.609   0.430   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.276   1.201   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.059   0.433   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.391   1.205   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.726   0.436   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.059   1.208   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.393   0.439   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.726   1.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.061   0.442   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.393   1.214   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.060  -1.107   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.728  -1.104   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       5.057   2.748   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      11.728   0.446   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   19                                                       
CONECT   16    8                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0015385
HETATM    1  C1  UNL     1       1.591  -0.486   1.262  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.406  -0.124  -0.180  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.705  -0.342  -0.923  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.725   0.539  -0.283  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.921   1.828  -0.734  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.848   2.688  -0.183  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.603   2.202   0.876  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.420   0.916   1.340  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.485   0.074   0.770  1.00  0.00           C  
HETATM   10  N1  UNL     1       0.315  -0.881  -0.763  1.00  0.00           N  
HETATM   11  C10 UNL     1      -0.841  -0.240  -1.268  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.905   1.011  -1.201  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.927  -1.036  -1.851  1.00  0.00           C  
HETATM   14  N2  UNL     1      -1.592  -2.425  -1.799  1.00  0.00           N  
HETATM   15  C12 UNL     1      -3.266  -0.746  -1.173  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.125  -1.090   0.281  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.382  -0.849   1.069  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.841   0.570   1.043  1.00  0.00           C  
HETATM   19  N3  UNL     1      -3.826   1.447   1.598  1.00  0.00           N  
HETATM   20  H1  UNL     1       2.023  -1.498   1.373  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.223   0.294   1.737  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.591  -0.508   1.771  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.133   0.946  -0.228  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.006  -1.390  -0.738  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.635  -0.176  -1.998  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.300   2.157  -1.568  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.964   3.690  -0.571  1.00  0.00           H  
HETATM   28  H9  UNL     1       6.322   2.883   1.297  1.00  0.00           H  
HETATM   29  H10 UNL     1       6.029   0.574   2.166  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.351  -0.948   1.150  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.376  -1.940  -0.816  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.051  -0.676  -2.914  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.348  -3.029  -1.400  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.451  -2.783  -2.792  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.032  -1.308  -1.704  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.452   0.330  -1.308  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.839  -2.152   0.384  1.00  0.00           H  
HETATM   38  H19 UNL     1      -2.301  -0.477   0.697  1.00  0.00           H  
HETATM   39  H20 UNL     1      -5.202  -1.498   0.715  1.00  0.00           H  
HETATM   40  H21 UNL     1      -4.197  -1.128   2.127  1.00  0.00           H  
HETATM   41  H22 UNL     1      -5.168   0.907   0.035  1.00  0.00           H  
HETATM   42  H23 UNL     1      -5.735   0.649   1.695  1.00  0.00           H  
HETATM   43  H24 UNL     1      -4.261   2.155   2.218  1.00  0.00           H  
HETATM   44  H25 UNL     1      -3.231   1.871   0.867  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   10   23
CONECT    3    4   24   25
CONECT    4    5    5    9
CONECT    5    6   26
CONECT    6    7    7   27
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   30
CONECT   10   11   31
CONECT   11   12   12   13
CONECT   13   14   15   32
CONECT   14   33   34
CONECT   15   16   35   36
CONECT   16   17   37   38
CONECT   17   18   39   40
CONECT   18   19   41   42
CONECT   19   43   44
END

HMDB0015385
     RDKit          3D
Lisdexamfetamine
 44 44  0  0  0  0  0  0  0  0999 V2000
    1.5914   -0.4858    1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -0.1235   -0.1799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7052   -0.3424   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7252    0.5386   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9213    1.8280   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    2.6877   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033    2.2024    0.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4203    0.9157    1.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854    0.0742    0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3153   -0.8815   -0.7629 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8408   -0.2398   -1.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    1.0111   -1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.0359   -1.8511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5923   -2.4252   -1.7993 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2659   -0.7461   -1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246   -1.0898    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3821   -0.8490    1.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411    0.5703    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255    1.4466    1.5977 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -1.4985    1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233    0.2936    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5908   -0.5078    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329    0.9456   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -1.3902   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354   -0.1759   -1.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    2.1571   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644    3.6900   -0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3220    2.8826    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285    0.5744    2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.9481    1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762   -1.9400   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0513   -0.6757   -2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482   -3.0289   -1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -2.7834   -2.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0322   -1.3079   -1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519    0.3300   -1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394   -2.1515    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -0.4767    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2022   -1.4985    0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972   -1.1277    2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1680    0.9070    0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353    0.6491    1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2613    2.1547    2.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2313    1.8714    0.8668 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  2  0
  2 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  9  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  6
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lisdexamfetamine dimesylate	HMDB
NRP104	HMDB
Vyvanse	HMDB
Lis dexamfetamine dimesylate	HMDB
NRP 104	HMDB
Elvanse	HMDB
Lis-dexamfetamine dimesylate	HMDB
Dimesylate, lis-dexamfetamine	HMDB
Dimesylate, lisdexamfetamine	HMDB
NRP-104	HMDB

Chemical Formula

C₁₅H₂₅N₃O

Average Molecular Weight

263.3785

Monoisotopic Molecular Weight

263.199762437

IUPAC Name

(2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide

Traditional Name

vyvanse

CAS Registry Number

608137-32-2

SMILES

C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN

InChI Identifier

InChI=1S/C15H25N3O/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19)/t12-,14-/m0/s1

InChI Key

VOBHXZCDAVEXEY-JSGCOSHPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Amphetamine or derivatives
Phenylpropane
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
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: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015385)

Source

Exogenous

Exogenous (HMDB: HMDB0015385)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.088 g/L	Not Available
LogP	1.06	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.14	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	15.89	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.14 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	78.31 m³·mol⁻¹	ChemAxon
Polarizability	31.28 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
DarkChem	[M+H]+	164.053	31661259
DarkChem	[M-H]-	163.373	31661259
DeepCCS	[M+H]+	167.09	30932474
DeepCCS	[M-H]-	164.693	30932474
DeepCCS	[M-2H]-	198.266	30932474
DeepCCS	[M+Na]+	173.473	30932474
AllCCS	[M+H]+	165.9	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.7	32859911
AllCCS	[M-H]-	167.5	32859911
AllCCS	[M+Na-2H]-	168.1	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lisdexamfetamine	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN	3228.3	Standard polar	33892256
Lisdexamfetamine	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN	2262.4	Standard non polar	33892256
Lisdexamfetamine	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN	2324.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lisdexamfetamine,1TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N[Si](C)(C)C	2378.6	Semi standard non polar	33892256
Lisdexamfetamine,1TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N[Si](C)(C)C	2332.9	Standard non polar	33892256
Lisdexamfetamine,1TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N[Si](C)(C)C	3402.9	Standard polar	33892256
Lisdexamfetamine,1TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN[Si](C)(C)C	2435.2	Semi standard non polar	33892256
Lisdexamfetamine,1TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN[Si](C)(C)C	2316.7	Standard non polar	33892256
Lisdexamfetamine,1TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN[Si](C)(C)C	3581.5	Standard polar	33892256
Lisdexamfetamine,1TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN)[Si](C)(C)C	2268.0	Semi standard non polar	33892256
Lisdexamfetamine,1TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN)[Si](C)(C)C	2325.6	Standard non polar	33892256
Lisdexamfetamine,1TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN)[Si](C)(C)C	3708.9	Standard polar	33892256
Lisdexamfetamine,2TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C)N[Si](C)(C)C	2466.3	Semi standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C)N[Si](C)(C)C	2445.9	Standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C)N[Si](C)(C)C	3015.3	Standard polar	33892256
Lisdexamfetamine,2TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N[Si](C)(C)C)[Si](C)(C)C	2341.7	Semi standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N[Si](C)(C)C)[Si](C)(C)C	2435.2	Standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N[Si](C)(C)C)[Si](C)(C)C	3197.9	Standard polar	33892256
Lisdexamfetamine,2TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C	2458.8	Semi standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C	2470.3	Standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C	3253.9	Standard polar	33892256
Lisdexamfetamine,2TMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN[Si](C)(C)C)[Si](C)(C)C	2394.6	Semi standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN[Si](C)(C)C)[Si](C)(C)C	2459.1	Standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN[Si](C)(C)C)[Si](C)(C)C	3236.3	Standard polar	33892256
Lisdexamfetamine,2TMS,isomer #5	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C	2582.6	Semi standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #5	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C	2470.2	Standard non polar	33892256
Lisdexamfetamine,2TMS,isomer #5	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C	3499.2	Standard polar	33892256
Lisdexamfetamine,3TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2436.4	Semi standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2543.2	Standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2827.4	Standard polar	33892256
Lisdexamfetamine,3TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2601.4	Semi standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2564.6	Standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2937.3	Standard polar	33892256
Lisdexamfetamine,3TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2555.5	Semi standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2573.9	Standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2873.4	Standard polar	33892256
Lisdexamfetamine,3TMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2464.1	Semi standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2561.0	Standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3092.5	Standard polar	33892256
Lisdexamfetamine,3TMS,isomer #5	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2552.7	Semi standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #5	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2602.6	Standard non polar	33892256
Lisdexamfetamine,3TMS,isomer #5	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3182.7	Standard polar	33892256
Lisdexamfetamine,4TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2598.0	Semi standard non polar	33892256
Lisdexamfetamine,4TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2647.6	Standard non polar	33892256
Lisdexamfetamine,4TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	2763.9	Standard polar	33892256
Lisdexamfetamine,4TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2585.7	Semi standard non polar	33892256
Lisdexamfetamine,4TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2656.7	Standard non polar	33892256
Lisdexamfetamine,4TMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2717.3	Standard polar	33892256
Lisdexamfetamine,4TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2733.5	Semi standard non polar	33892256
Lisdexamfetamine,4TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2686.6	Standard non polar	33892256
Lisdexamfetamine,4TMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2815.1	Standard polar	33892256
Lisdexamfetamine,5TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2821.5	Semi standard non polar	33892256
Lisdexamfetamine,5TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2769.8	Standard non polar	33892256
Lisdexamfetamine,5TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2685.6	Standard polar	33892256
Lisdexamfetamine,1TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N[Si](C)(C)C(C)(C)C	2588.2	Semi standard non polar	33892256
Lisdexamfetamine,1TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N[Si](C)(C)C(C)(C)C	2548.8	Standard non polar	33892256
Lisdexamfetamine,1TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N[Si](C)(C)C(C)(C)C	3420.9	Standard polar	33892256
Lisdexamfetamine,1TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN[Si](C)(C)C(C)(C)C	2641.2	Semi standard non polar	33892256
Lisdexamfetamine,1TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN[Si](C)(C)C(C)(C)C	2520.5	Standard non polar	33892256
Lisdexamfetamine,1TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN[Si](C)(C)C(C)(C)C	3618.5	Standard polar	33892256
Lisdexamfetamine,1TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN)[Si](C)(C)C(C)(C)C	2520.7	Semi standard non polar	33892256
Lisdexamfetamine,1TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN)[Si](C)(C)C(C)(C)C	2549.3	Standard non polar	33892256
Lisdexamfetamine,1TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN)[Si](C)(C)C(C)(C)C	3725.9	Standard polar	33892256
Lisdexamfetamine,2TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2885.8	Semi standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2816.2	Standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3149.0	Standard polar	33892256
Lisdexamfetamine,2TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2818.6	Semi standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2819.9	Standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3287.0	Standard polar	33892256
Lisdexamfetamine,2TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2891.9	Semi standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2825.5	Standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3300.6	Standard polar	33892256
Lisdexamfetamine,2TBDMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2859.4	Semi standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2842.4	Standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3341.2	Standard polar	33892256
Lisdexamfetamine,2TBDMS,isomer #5	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2995.2	Semi standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #5	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2804.5	Standard non polar	33892256
Lisdexamfetamine,2TBDMS,isomer #5	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3511.9	Standard polar	33892256
Lisdexamfetamine,3TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3101.0	Semi standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3042.7	Standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3104.1	Standard polar	33892256
Lisdexamfetamine,3TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3252.5	Semi standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3058.8	Standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3158.4	Standard polar	33892256
Lisdexamfetamine,3TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3227.0	Semi standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3058.3	Standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3105.6	Standard polar	33892256
Lisdexamfetamine,3TBDMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3139.6	Semi standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3059.9	Standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #4	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3229.6	Standard polar	33892256
Lisdexamfetamine,3TBDMS,isomer #5	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3214.0	Semi standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #5	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3079.3	Standard non polar	33892256
Lisdexamfetamine,3TBDMS,isomer #5	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3341.2	Standard polar	33892256
Lisdexamfetamine,4TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3473.0	Semi standard non polar	33892256
Lisdexamfetamine,4TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3288.8	Standard non polar	33892256
Lisdexamfetamine,4TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3091.0	Standard polar	33892256
Lisdexamfetamine,4TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3473.4	Semi standard non polar	33892256
Lisdexamfetamine,4TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3287.5	Standard non polar	33892256
Lisdexamfetamine,4TBDMS,isomer #2	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3058.8	Standard polar	33892256
Lisdexamfetamine,4TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3568.5	Semi standard non polar	33892256
Lisdexamfetamine,4TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3289.6	Standard non polar	33892256
Lisdexamfetamine,4TBDMS,isomer #3	C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3088.3	Standard polar	33892256
Lisdexamfetamine,5TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3810.2	Semi standard non polar	33892256
Lisdexamfetamine,5TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3512.7	Standard non polar	33892256
Lisdexamfetamine,5TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N(C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3081.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lisdexamfetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-7910000000-cf67fb00e86045c2e167	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lisdexamfetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 10V, Positive-QTOF	splash10-01qa-1980000000-d55cfea0090eb8a203ec	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 20V, Positive-QTOF	splash10-001i-3910000000-6c0e093306cb1a142d27	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 40V, Positive-QTOF	splash10-00lr-9600000000-0319b363d14e7fb37bdb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 10V, Negative-QTOF	splash10-03di-0290000000-3d4c25de9940b1f84b65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 20V, Negative-QTOF	splash10-01sl-1940000000-934e79a23f532e705cd7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 40V, Negative-QTOF	splash10-00lu-4900000000-c557594a41309e8f3655	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 10V, Positive-QTOF	splash10-03di-0090000000-378898bcf4a9421cb8d5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 20V, Positive-QTOF	splash10-01ql-9780000000-45bb7d0848ffcb464b5b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 40V, Positive-QTOF	splash10-0006-9100000000-4e7bbad339ecdb03e6c4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 10V, Negative-QTOF	splash10-03di-0090000000-45f7796828e5f04a3c2f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 20V, Negative-QTOF	splash10-01t9-6920000000-8183a8d18b1b49ca7221	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisdexamfetamine 40V, Negative-QTOF	splash10-0006-9100000000-7d80f02475e4b0ca64f3	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB01255	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01255	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01255

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9772458

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lisdexamfetamine

METLIN ID

Not Available

PubChem Compound

11597698

PDB ID

Not Available

ChEBI ID

775173

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

Krishnan S, Moncrief S: An evaluation of the cytochrome p450 inhibition potential of lisdexamfetamine in human liver microsomes. Drug Metab Dispos. 2007 Jan;35(1):180-4. Epub 2006 Oct 11. [PubMed:17035599 ]
Madaan V: Lisdexamfetamine dimesylate for childhood ADHD. Drugs Today (Barc). 2008 May;44(5):319-24. doi: 10.1358/dot.2008.44.5.1215724. [PubMed:18548134 ]
Jasinski DR, Krishnan S: Human pharmacology of intravenous lisdexamfetamine dimesylate: abuse liability in adult stimulant abusers. J Psychopharmacol. 2009 Jun;23(4):410-8. doi: 10.1177/0269881108093841. Epub 2008 Jul 17. [PubMed:18635707 ]

Enzymes

Enzyme Details

1. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Hamidovic A, Dlugos A, Palmer AA, de Wit H: Polymorphisms in dopamine transporter (SLC6A3) are associated with stimulant effects of D-amphetamine: an exploratory pharmacogenetic study using healthy volunteers. Behav Genet. 2010 Mar;40(2):255-61. doi: 10.1007/s10519-009-9331-7. Epub 2010 Jan 21. [PubMed:20091113 ]

Enzyme Details

2. Alpha-1B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Lisdexamfetamine (HMDB0015385)

MOL for HMDB0015385 (Lisdexamfetamine)

3D MOL for HMDB0015385 (Lisdexamfetamine)

3D SDF for HMDB0015385 (Lisdexamfetamine)

3D-SDF for HMDB0015385 (Lisdexamfetamine)

PDB for HMDB0015385 (Lisdexamfetamine)

3D PDB for HMDB0015385 (Lisdexamfetamine)

SMILES for HMDB0015385 (Lisdexamfetamine)

INCHI for HMDB0015385 (Lisdexamfetamine)

Structure for HMDB0015385 (Lisdexamfetamine)

3D Structure for HMDB0015385 (Lisdexamfetamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References