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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:46:41 UTC

Update Date

2021-09-26 23:07:27 UTC

HMDB ID

HMDB0253881

Secondary Accession Numbers

None

Metabolite Identification

Common Name

L-DOPA n-Butyl Ester

Description

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

HMDB0253881
     RDKit          3D
L-DOPA n-Butyl Ester
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.9542    0.0105   -0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559    0.4142    0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.7561    1.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -0.3827    2.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1872    0.6052    1.7841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    0.5772    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926   -0.4708    0.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.6746    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    2.7320    1.4657 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272    1.2632    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096    0.1354   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3567   -1.1585    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -2.2382   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2226   -1.9794   -1.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5891   -3.0375   -2.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885   -0.6958   -2.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -0.5107   -3.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250    0.3348   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -1.0350   -0.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877    0.6578   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0030   -0.0186   -0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3673    1.2548    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5414    0.7742    1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7900   -1.4945    1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765   -1.2988    0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6577   -0.0848    2.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5360   -1.3051    2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441    2.0369   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    3.2684    1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    3.2824    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    2.1165    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889    1.0531    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -1.3881    1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5983   -3.2620   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9640   -2.8802   -3.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0093    0.4625   -3.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558    1.3428   -1.7690 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
M  END


  Mrv1652309112114462D          

 18 18  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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   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
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    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
  3  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 12 17  1  0  0  0  0
  8 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253881

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO4/c1-2-3-6-18-13(17)10(14)7-9-4-5-11(15)12(16)8-9/h4-5,8,10,15-16H,2-3,6-7,14H2,1H3

> <INCHI_KEY>
QDMOINLDXCZCEK-UHFFFAOYSA-N

> <FORMULA>
C13H19NO4

> <MOLECULAR_WEIGHT>
253.298

> <EXACT_MASS>
253.131408096

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.284621197602725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
butyl 2-amino-3-(3,4-dihydroxyphenyl)propanoate

> <ALOGPS_LOGP>
1.07

> <JCHEM_LOGP>
1.9402774803333334

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.735157430743715

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.287383490873005

> <JCHEM_PKA_STRONGEST_BASIC>
6.970797470191192

> <JCHEM_POLAR_SURFACE_AREA>
92.78

> <JCHEM_REFRACTIVITY>
67.72080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl 2-amino-3-(3,4-dihydroxyphenyl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253881
     RDKit          3D
L-DOPA n-Butyl Ester
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.9542    0.0105   -0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559    0.4142    0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.7561    1.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -0.3827    2.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1872    0.6052    1.7841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    0.5772    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926   -0.4708    0.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.6746    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    2.7320    1.4657 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272    1.2632    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096    0.1354   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3567   -1.1585    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -2.2382   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2226   -1.9794   -1.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5891   -3.0375   -2.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885   -0.6958   -2.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -0.5107   -3.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250    0.3348   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -1.0350   -0.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877    0.6578   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0030   -0.0186   -0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3673    1.2548    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5414    0.7742    1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7900   -1.4945    1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765   -1.2988    0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6577   -0.0848    2.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5360   -1.3051    2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441    2.0369   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    3.2684    1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    3.2824    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    2.1165    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889    1.0531    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -1.3881    1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5983   -3.2620   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9640   -2.8802   -3.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0093    0.4625   -3.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558    1.3428   -1.7690 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  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       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      18.672  -9.240   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      12.003 -11.550   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13                                                            
CONECT   17   12                                                            
CONECT   18    8                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0253881
HETATM    1  C1  UNL     1       4.954   0.010  -0.433  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.956   0.414   0.631  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.080  -0.756   1.040  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.097  -0.383   2.077  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.187   0.605   1.784  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.257   0.577   0.758  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.293  -0.471   0.063  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.700   1.675   0.490  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.376   2.732   1.466  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.127   1.263   0.737  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.510   0.135  -0.122  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.357  -1.159   0.326  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.714  -2.238  -0.486  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.223  -1.979  -1.743  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.589  -3.038  -2.578  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.388  -0.696  -2.221  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.906  -0.511  -3.496  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.025   0.335  -1.392  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.725  -1.035  -0.741  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.888   0.658  -1.333  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.003  -0.019  -0.031  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.367   1.255   0.226  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.541   0.774   1.494  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.790  -1.494   1.524  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.676  -1.299   0.170  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.658  -0.085   2.997  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.536  -1.305   2.372  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.544   2.037  -0.535  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.453   3.268   1.188  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.204   3.282   1.729  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.813   2.116   0.509  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.289   1.053   1.819  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.969  -1.388   1.293  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.598  -3.262  -0.144  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.964  -2.880  -3.503  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.009   0.462  -3.804  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.156   1.343  -1.769  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10   28
CONECT    9   29   30
CONECT   10   11   31   32
CONECT   11   12   12   18
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   16
CONECT   15   35
CONECT   16   17   18   18
CONECT   17   36
CONECT   18   37
END

HMDB0253881
     RDKit          3D
L-DOPA n-Butyl Ester
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.9542    0.0105   -0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559    0.4142    0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.7561    1.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -0.3827    2.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1872    0.6052    1.7841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    0.5772    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926   -0.4708    0.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.6746    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    2.7320    1.4657 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272    1.2632    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096    0.1354   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3567   -1.1585    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -2.2382   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2226   -1.9794   -1.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5891   -3.0375   -2.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885   -0.6958   -2.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -0.5107   -3.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250    0.3348   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -1.0350   -0.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877    0.6578   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0030   -0.0186   -0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3673    1.2548    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5414    0.7742    1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7900   -1.4945    1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765   -1.2988    0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6577   -0.0848    2.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5360   -1.3051    2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441    2.0369   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    3.2684    1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    3.2824    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    2.1165    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889    1.0531    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -1.3881    1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5983   -3.2620   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9640   -2.8802   -3.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0093    0.4625   -3.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558    1.3428   -1.7690 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₉NO₄

Average Molecular Weight

253.298

Monoisotopic Molecular Weight

253.131408096

IUPAC Name

butyl 2-amino-3-(3,4-dihydroxyphenyl)propanoate

Traditional Name

butyl 2-amino-3-(3,4-dihydroxyphenyl)propanoate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)C(N)CC1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C13H19NO4/c1-2-3-6-18-13(17)10(14)7-9-4-5-11(15)12(16)8-9/h4-5,8,10,15-16H,2-3,6-7,14H2,1H3

InChI Key

QDMOINLDXCZCEK-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
Alpha-amino acid ester
Amphetamine or derivatives
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Organic nitrogen compound
Amine
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	1.07	ALOGPS
logP	1.94	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	6.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	67.72 m³·mol⁻¹	ChemAxon
Polarizability	27.28 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
DeepCCS	[M+H]+	167.814	30932474
DeepCCS	[M-H]-	165.456	30932474
DeepCCS	[M-2H]-	198.342	30932474
DeepCCS	[M+Na]+	173.907	30932474
AllCCS	[M+H]+	159.7	32859911
AllCCS	[M+H-H2O]+	156.3	32859911
AllCCS	[M+NH4]+	162.9	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	161.8	32859911
AllCCS	[M+HCOO]-	162.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-DOPA n-Butyl Ester	CCCCOC(=O)C(N)CC1=CC(O)=C(O)C=C1	3409.0	Standard polar	33892256
L-DOPA n-Butyl Ester	CCCCOC(=O)C(N)CC1=CC(O)=C(O)C=C1	2364.7	Standard non polar	33892256
L-DOPA n-Butyl Ester	CCCCOC(=O)C(N)CC1=CC(O)=C(O)C=C1	2159.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-DOPA n-Butyl Ester,3TMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N[Si](C)(C)C	2259.9	Semi standard non polar	33892256
L-DOPA n-Butyl Ester,3TMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N[Si](C)(C)C	2253.5	Standard non polar	33892256
L-DOPA n-Butyl Ester,3TMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N[Si](C)(C)C	2493.7	Standard polar	33892256
L-DOPA n-Butyl Ester,3TMS,isomer #2	CCCCOC(=O)C(CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2391.4	Semi standard non polar	33892256
L-DOPA n-Butyl Ester,3TMS,isomer #2	CCCCOC(=O)C(CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2391.8	Standard non polar	33892256
L-DOPA n-Butyl Ester,3TMS,isomer #2	CCCCOC(=O)C(CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2659.3	Standard polar	33892256
L-DOPA n-Butyl Ester,3TMS,isomer #3	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2408.6	Semi standard non polar	33892256
L-DOPA n-Butyl Ester,3TMS,isomer #3	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2377.4	Standard non polar	33892256
L-DOPA n-Butyl Ester,3TMS,isomer #3	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	2628.6	Standard polar	33892256
L-DOPA n-Butyl Ester,4TMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2495.3	Semi standard non polar	33892256
L-DOPA n-Butyl Ester,4TMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2352.3	Standard non polar	33892256
L-DOPA n-Butyl Ester,4TMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	2428.9	Standard polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N[Si](C)(C)C(C)(C)C	2951.4	Semi standard non polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N[Si](C)(C)C(C)(C)C	2811.8	Standard non polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N[Si](C)(C)C(C)(C)C	2846.5	Standard polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #2	CCCCOC(=O)C(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3087.6	Semi standard non polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #2	CCCCOC(=O)C(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2951.1	Standard non polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #2	CCCCOC(=O)C(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2919.4	Standard polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #3	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3128.3	Semi standard non polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #3	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2927.9	Standard non polar	33892256
L-DOPA n-Butyl Ester,3TBDMS,isomer #3	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2890.3	Standard polar	33892256
L-DOPA n-Butyl Ester,4TBDMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3393.6	Semi standard non polar	33892256
L-DOPA n-Butyl Ester,4TBDMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3045.0	Standard non polar	33892256
L-DOPA n-Butyl Ester,4TBDMS,isomer #1	CCCCOC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2837.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2900000000-a5bfde5d2c95d1928fb8	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-DOPA n-Butyl Ester GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-04	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 - L-DOPA n-Butyl Ester 10V, Positive-QTOF	splash10-0udi-0590000000-7aaacc74e3cfcb1e80b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-DOPA n-Butyl Ester 20V, Positive-QTOF	splash10-0udi-2900000000-e76f185fbf373b5b628a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-DOPA n-Butyl Ester 40V, Positive-QTOF	splash10-0a4i-8900000000-8fc6cb5ce03122672ef3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-DOPA n-Butyl Ester 10V, Negative-QTOF	splash10-0udi-0090000000-c982327c982780b0f07f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-DOPA n-Butyl Ester 20V, Negative-QTOF	splash10-00di-3930000000-cd98001b28029c5ecb9c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-DOPA n-Butyl Ester 40V, Negative-QTOF	splash10-00di-4900000000-79c1749cfb15ad51605c	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

10440098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23274845

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 L-DOPA n-Butyl Ester (HMDB0253881)

MOL for HMDB0253881 (L-DOPA n-Butyl Ester)

3D MOL for HMDB0253881 (L-DOPA n-Butyl Ester)

3D SDF for HMDB0253881 (L-DOPA n-Butyl Ester)

3D-SDF for HMDB0253881 (L-DOPA n-Butyl Ester)

PDB for HMDB0253881 (L-DOPA n-Butyl Ester)

3D PDB for HMDB0253881 (L-DOPA n-Butyl Ester)

SMILES for HMDB0253881 (L-DOPA n-Butyl Ester)

INCHI for HMDB0253881 (L-DOPA n-Butyl Ester)

Structure for HMDB0253881 (L-DOPA n-Butyl Ester)

3D Structure for HMDB0253881 (L-DOPA n-Butyl Ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra