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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:20:28 UTC

Update Date

2021-09-26 22:56:58 UTC

HMDB ID

HMDB0247332

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Leucine-beta-naphthylamide

Description

Leucine-beta-naphthylamide, also known as leu-nap or N-L-leucyl-2-naphthylamine, belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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 a significant number of articles have been published on Leucine-beta-naphthylamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Leucine-beta-naphthylamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Leucine-beta-naphthylamide 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

HMDB0247332
     RDKit          3D
Leucine-beta-naphthylamide
 39 40  0  0  0  0  0  0  0  0999 V2000
   -5.3234    0.8877   -1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4599    0.6153   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8960   -0.6263    0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035    0.5866   -0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523    0.3202    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654   -0.9094    1.2613 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949    0.4511    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788    1.4830   -0.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -0.5449    0.6073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192   -0.5299    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.6303    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253   -1.7055    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3727   -0.7033   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7254   -0.7737   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3746    0.2435   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838    1.3402   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    1.4126   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6890    0.3874   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066    0.4517   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605    1.6848   -2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220    1.1988   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5022   -0.0482   -2.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6370    1.4776    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4415   -1.5507    0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0214   -0.6549    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6830   -0.4813    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -0.2343   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    1.5060   -1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366    1.1441    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.9027    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -1.7674    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012   -1.3740    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8519   -2.4309    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2898   -2.5518    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2644   -1.6375    0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.1784   -1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2338    2.1177   -1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817    2.2618   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    1.3084   -0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 10  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
M  END


  Mrv1652309112102202D          

 19 20  0  0  0  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    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
    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 O   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
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  0  0  0  0
  5 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247332

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(N)C(=O)NC1=CC2=CC=CC=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O/c1-11(2)9-15(17)16(19)18-14-8-7-12-5-3-4-6-13(12)10-14/h3-8,10-11,15H,9,17H2,1-2H3,(H,18,19)

> <INCHI_KEY>
JWHURRLUBVMKOT-UHFFFAOYSA-N

> <FORMULA>
C16H20N2O

> <MOLECULAR_WEIGHT>
256.349

> <EXACT_MASS>
256.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.890608608544916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-4-methyl-N-(naphthalen-2-yl)pentanamide

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
3.0991774960000003

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.236425872389166

> <JCHEM_PKA_STRONGEST_BASIC>
8.271329292757102

> <JCHEM_POLAR_SURFACE_AREA>
55.120000000000005

> <JCHEM_REFRACTIVITY>
78.89840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-methyl-N-(naphthalen-2-yl)pentanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247332
     RDKit          3D
Leucine-beta-naphthylamide
 39 40  0  0  0  0  0  0  0  0999 V2000
   -5.3234    0.8877   -1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4599    0.6153   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8960   -0.6263    0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035    0.5866   -0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523    0.3202    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654   -0.9094    1.2613 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949    0.4511    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788    1.4830   -0.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -0.5449    0.6073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192   -0.5299    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.6303    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253   -1.7055    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3727   -0.7033   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7254   -0.7737   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3746    0.2435   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838    1.3402   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    1.4126   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6890    0.3874   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066    0.4517   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605    1.6848   -2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220    1.1988   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5022   -0.0482   -2.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6370    1.4776    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4415   -1.5507    0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0214   -0.6549    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6830   -0.4813    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -0.2343   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    1.5060   -1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366    1.1441    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.9027    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -1.7674    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012   -1.3740    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8519   -2.4309    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2898   -2.5518    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2644   -1.6375    0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.1784   -1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2338    2.1177   -1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817    2.2618   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    1.3084   -0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 10  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      10.669  -9.240   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.002  -7.700   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    9                                                       
CONECT   19    5                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0247332
HETATM    1  C1  UNL     1      -5.323   0.888  -1.495  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.460   0.615  -0.284  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.896  -0.626   0.439  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.003   0.587  -0.607  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.152   0.320   0.583  1.00  0.00           C  
HETATM    6  N1  UNL     1      -2.365  -0.909   1.261  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.695   0.451   0.244  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.379   1.483  -0.369  1.00  0.00           O  
HETATM    9  N2  UNL     1       0.236  -0.545   0.607  1.00  0.00           N  
HETATM   10  C7  UNL     1       1.619  -0.530   0.344  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.364  -1.630   0.795  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.725  -1.705   0.583  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.373  -0.703  -0.072  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.725  -0.774  -0.284  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.375   0.244  -0.948  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.684   1.340  -1.407  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.326   1.413  -1.195  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.689   0.387  -0.529  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.307   0.452  -0.308  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.860   1.685  -2.080  1.00  0.00           H  
HETATM   21  H2  UNL     1      -6.322   1.199  -1.126  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.502  -0.048  -2.085  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.637   1.478   0.417  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.441  -1.551   0.081  1.00  0.00           H  
HETATM   25  H6  UNL     1      -6.021  -0.655   0.339  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.683  -0.481   1.535  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.825  -0.234  -1.354  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.656   1.506  -1.112  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.337   1.144   1.333  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.187  -0.903   2.268  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.156  -1.767   0.750  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.201  -1.374   1.135  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.852  -2.431   1.317  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.290  -2.552   0.932  1.00  0.00           H  
HETATM   35  H16 UNL     1       6.264  -1.637   0.078  1.00  0.00           H  
HETATM   36  H17 UNL     1       7.462   0.178  -1.114  1.00  0.00           H  
HETATM   37  H18 UNL     1       6.234   2.118  -1.925  1.00  0.00           H  
HETATM   38  H19 UNL     1       3.782   2.262  -1.549  1.00  0.00           H  
HETATM   39  H20 UNL     1       1.798   1.308  -0.673  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4   23
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6    7   29
CONECT    6   30   31
CONECT    7    8    8    9
CONECT    9   10   32
CONECT   10   11   11   19
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   18
CONECT   14   15   15   35
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   38
CONECT   18   19   19
CONECT   19   39
END

HMDB0247332
     RDKit          3D
Leucine-beta-naphthylamide
 39 40  0  0  0  0  0  0  0  0999 V2000
   -5.3234    0.8877   -1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4599    0.6153   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8960   -0.6263    0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035    0.5866   -0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523    0.3202    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654   -0.9094    1.2613 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949    0.4511    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788    1.4830   -0.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -0.5449    0.6073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192   -0.5299    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.6303    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253   -1.7055    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3727   -0.7033   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7254   -0.7737   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3746    0.2435   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838    1.3402   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    1.4126   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6890    0.3874   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066    0.4517   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605    1.6848   -2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220    1.1988   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5022   -0.0482   -2.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6370    1.4776    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4415   -1.5507    0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0214   -0.6549    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6830   -0.4813    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -0.2343   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    1.5060   -1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366    1.1441    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.9027    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -1.7674    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012   -1.3740    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8519   -2.4309    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2898   -2.5518    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2644   -1.6375    0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.1784   -1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2338    2.1177   -1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817    2.2618   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    1.3084   -0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 10  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Leucine-b-naphthylamide	Generator
Leucine-β-naphthylamide	Generator
Leu-nap	HMDB
N-L-Leucyl-2-naphthylamine	HMDB
Leucine-2-naphthylamide	HMDB

Chemical Formula

C₁₆H₂₀N₂O

Average Molecular Weight

256.349

Monoisotopic Molecular Weight

256.157563272

IUPAC Name

2-amino-4-methyl-N-(naphthalen-2-yl)pentanamide

Traditional Name

2-amino-4-methyl-N-(naphthalen-2-yl)pentanamide

CAS Registry Number

Not Available

SMILES

CC(C)CC(N)C(=O)NC1=CC2=CC=CC=C2C=C1

InChI Identifier

InChI=1S/C16H20N2O/c1-11(2)9-15(17)16(19)18-14-8-7-12-5-3-4-6-13(12)10-14/h3-8,10-11,15H,9,17H2,1-2H3,(H,18,19)

InChI Key

JWHURRLUBVMKOT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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

Leucine and derivatives

Alternative Parents

Substituents

Leucine or derivatives
Alpha-amino acid amide
Naphthalene
N-arylamide
Fatty amide
Fatty acyl
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.57	ALOGPS
logP	3.1	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.9 m³·mol⁻¹	ChemAxon
Polarizability	29.89 Å³	ChemAxon
Number of Rings	2	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]+	171.674	30932474
DeepCCS	[M-H]-	169.316	30932474
DeepCCS	[M-2H]-	202.202	30932474
DeepCCS	[M+Na]+	177.767	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.7	32859911
AllCCS	[M+NH4]+	165.3	32859911
AllCCS	[M+Na]+	166.2	32859911
AllCCS	[M-H]-	165.8	32859911
AllCCS	[M+Na-2H]-	165.9	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leucine-beta-naphthylamide	CC(C)CC(N)C(=O)NC1=CC2=CC=CC=C2C=C1	3139.2	Standard polar	33892256
Leucine-beta-naphthylamide	CC(C)CC(N)C(=O)NC1=CC2=CC=CC=C2C=C1	2201.2	Standard non polar	33892256
Leucine-beta-naphthylamide	CC(C)CC(N)C(=O)NC1=CC2=CC=CC=C2C=C1	2438.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leucine-beta-naphthylamide,1TMS,isomer #1	CC(C)CC(N[Si](C)(C)C)C(=O)NC1=CC=C2C=CC=CC2=C1	2359.6	Semi standard non polar	33892256
Leucine-beta-naphthylamide,1TMS,isomer #1	CC(C)CC(N[Si](C)(C)C)C(=O)NC1=CC=C2C=CC=CC2=C1	2336.9	Standard non polar	33892256
Leucine-beta-naphthylamide,1TMS,isomer #1	CC(C)CC(N[Si](C)(C)C)C(=O)NC1=CC=C2C=CC=CC2=C1	3137.3	Standard polar	33892256
Leucine-beta-naphthylamide,1TMS,isomer #2	CC(C)CC(N)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C	2215.4	Semi standard non polar	33892256
Leucine-beta-naphthylamide,1TMS,isomer #2	CC(C)CC(N)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C	2314.6	Standard non polar	33892256
Leucine-beta-naphthylamide,1TMS,isomer #2	CC(C)CC(N)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C	3126.8	Standard polar	33892256
Leucine-beta-naphthylamide,2TMS,isomer #1	CC(C)CC(C(=O)NC1=CC=C2C=CC=CC2=C1)N([Si](C)(C)C)[Si](C)(C)C	2468.0	Semi standard non polar	33892256
Leucine-beta-naphthylamide,2TMS,isomer #1	CC(C)CC(C(=O)NC1=CC=C2C=CC=CC2=C1)N([Si](C)(C)C)[Si](C)(C)C	2482.7	Standard non polar	33892256
Leucine-beta-naphthylamide,2TMS,isomer #1	CC(C)CC(C(=O)NC1=CC=C2C=CC=CC2=C1)N([Si](C)(C)C)[Si](C)(C)C	3010.0	Standard polar	33892256
Leucine-beta-naphthylamide,2TMS,isomer #2	CC(C)CC(N[Si](C)(C)C)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C	2223.2	Semi standard non polar	33892256
Leucine-beta-naphthylamide,2TMS,isomer #2	CC(C)CC(N[Si](C)(C)C)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C	2425.4	Standard non polar	33892256
Leucine-beta-naphthylamide,2TMS,isomer #2	CC(C)CC(N[Si](C)(C)C)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C	2800.1	Standard polar	33892256
Leucine-beta-naphthylamide,3TMS,isomer #1	CC(C)CC(C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2428.8	Semi standard non polar	33892256
Leucine-beta-naphthylamide,3TMS,isomer #1	CC(C)CC(C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2554.3	Standard non polar	33892256
Leucine-beta-naphthylamide,3TMS,isomer #1	CC(C)CC(C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2723.9	Standard polar	33892256
Leucine-beta-naphthylamide,1TBDMS,isomer #1	CC(C)CC(N[Si](C)(C)C(C)(C)C)C(=O)NC1=CC=C2C=CC=CC2=C1	2584.5	Semi standard non polar	33892256
Leucine-beta-naphthylamide,1TBDMS,isomer #1	CC(C)CC(N[Si](C)(C)C(C)(C)C)C(=O)NC1=CC=C2C=CC=CC2=C1	2548.5	Standard non polar	33892256
Leucine-beta-naphthylamide,1TBDMS,isomer #1	CC(C)CC(N[Si](C)(C)C(C)(C)C)C(=O)NC1=CC=C2C=CC=CC2=C1	3190.3	Standard polar	33892256
Leucine-beta-naphthylamide,1TBDMS,isomer #2	CC(C)CC(N)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C	2481.4	Semi standard non polar	33892256
Leucine-beta-naphthylamide,1TBDMS,isomer #2	CC(C)CC(N)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C	2516.7	Standard non polar	33892256
Leucine-beta-naphthylamide,1TBDMS,isomer #2	CC(C)CC(N)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C	3190.1	Standard polar	33892256
Leucine-beta-naphthylamide,2TBDMS,isomer #1	CC(C)CC(C(=O)NC1=CC=C2C=CC=CC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2933.1	Semi standard non polar	33892256
Leucine-beta-naphthylamide,2TBDMS,isomer #1	CC(C)CC(C(=O)NC1=CC=C2C=CC=CC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2867.4	Standard non polar	33892256
Leucine-beta-naphthylamide,2TBDMS,isomer #1	CC(C)CC(C(=O)NC1=CC=C2C=CC=CC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3105.6	Standard polar	33892256
Leucine-beta-naphthylamide,2TBDMS,isomer #2	CC(C)CC(N[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C	2668.4	Semi standard non polar	33892256
Leucine-beta-naphthylamide,2TBDMS,isomer #2	CC(C)CC(N[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C	2838.7	Standard non polar	33892256
Leucine-beta-naphthylamide,2TBDMS,isomer #2	CC(C)CC(N[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C	2986.8	Standard polar	33892256
Leucine-beta-naphthylamide,3TBDMS,isomer #1	CC(C)CC(C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3122.5	Semi standard non polar	33892256
Leucine-beta-naphthylamide,3TBDMS,isomer #1	CC(C)CC(C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3115.4	Standard non polar	33892256
Leucine-beta-naphthylamide,3TBDMS,isomer #1	CC(C)CC(C(=O)N(C1=CC=C2C=CC=CC2=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2968.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Leucine-beta-naphthylamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9510000000-cfbdd2770d4ba9742b55	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leucine-beta-naphthylamide 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 - Leucine-beta-naphthylamide 10V, Negative-QTOF	splash10-0a4i-0090000000-d58e919b02e6e2481eb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucine-beta-naphthylamide 20V, Negative-QTOF	splash10-0006-0910000000-dff580c00bf629219789	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucine-beta-naphthylamide 40V, Negative-QTOF	splash10-0006-0900000000-06bc9edee6c0c1ba61cd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucine-beta-naphthylamide 10V, Positive-QTOF	splash10-0a4i-1190000000-c3178ab2df9ca2a0586b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucine-beta-naphthylamide 20V, Positive-QTOF	splash10-052f-2690000000-8016cb1aaae7db8dc6b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucine-beta-naphthylamide 40V, Positive-QTOF	splash10-00kf-9610000000-ab3d69ce01260f33e371	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

369084

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

416927

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 Leucine-beta-naphthylamide (HMDB0247332)

MOL for HMDB0247332 (Leucine-beta-naphthylamide)

3D MOL for HMDB0247332 (Leucine-beta-naphthylamide)

3D SDF for HMDB0247332 (Leucine-beta-naphthylamide)

3D-SDF for HMDB0247332 (Leucine-beta-naphthylamide)

PDB for HMDB0247332 (Leucine-beta-naphthylamide)

3D PDB for HMDB0247332 (Leucine-beta-naphthylamide)

SMILES for HMDB0247332 (Leucine-beta-naphthylamide)

INCHI for HMDB0247332 (Leucine-beta-naphthylamide)

Structure for HMDB0247332 (Leucine-beta-naphthylamide)

3D Structure for HMDB0247332 (Leucine-beta-naphthylamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra