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Showing NP-Card for L-Dopa (NP0000605)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:41:52 UTC
NP-MRD IDNP0000605
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Dopa
DescriptionL-DOPA, also known as levodopa or 3,4-dihydroxyphenylalanine is an alpha amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-DOPA is found naturally in both animals and plants. It is made via biosynthesis from the amino acid L-tyrosine by the enzyme tyrosine hydroxylase.. L-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. The Swedish scientist Arvid Carlsson first showed in the 1950s that administering L-DOPA to animals with drug-induced (reserpine) Parkinsonian symptoms caused a reduction in the intensity of the animals' symptoms. Unlike dopamine itself, L-DOPA can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. In particular, it is metabolized to dopamine by aromatic L-amino acid decarboxylase. Pyridoxal phosphate (vitamin B6) is a required cofactor for this decarboxylation, and may be administered along with levodopa, usually as pyridoxine. As a result, L-DOPA is a drug that is now used for the treatment of Parkinsonian disorders and DOPA-Responsive Dystonia. It is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. It is standard clinical practice in treating Parkinsonism to co-administer a peripheral DOPA decarboxylase inhibitor - carbidopa or benserazide - and often a catechol-O-methyl transferase (COMT) inhibitor, to prevent synthesis of dopamine in peripheral tissue. Side effects of L-DOPA treatment may include: Hypertension, arrhythmias, nausea, gastrointestinal bleeding, disturbed respiration, hair loss, disorientation and confusion. L-DOPA can act as an L-tyrosine mimetic and be incorporated into proteins by mammalian cells in place of L-tyrosine, generating protease-resistant and aggregate-prone proteins in vitro and may contribute to neurotoxicity with chronic L-DOPA administration. L-phenylalanine, L-tyrosine, and L-DOPA are all precursors to the biological pigment melanin. The enzyme tyrosinase catalyzes the oxidation of L-DOPA to the reactive intermediate dopaquinone, which reacts further, eventually leading to melanin oligomers.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000605 (L-Dopa)


  Mrv1652309032023562D          

 14 14  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 12  2  1  0  0  0  0
 10  3  1  0  0  0  0
  4  3  1  0  0  0  0
  1  5  1  0  0  0  0
  5  3  2  0  0  0  0
  2 13  1  0  0  0  0
 13  4  2  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
 11  6  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
Download

3D MOL for NP0000605 (L-Dopa)

HMDB0000181
     RDKit          3D
L-Dopa
 25 25  0  0  0  0  0  0  0  0999 V2000
   -3.2741   -1.2218    0.9174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774   -0.4157    0.3941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9128   -1.0011    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3206   -0.3257    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719   -0.7684   -0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466   -0.1726   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6928    0.8912   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8612    1.4893   -0.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523    1.3472    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6205    2.4191    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    0.7409    1.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2205   -0.4472   -1.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0967   -1.1186   -1.6647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3048    0.2564   -1.8190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1285   -1.1606    0.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293   -2.2495    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3682    0.6171    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -2.0540    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870   -0.9902    2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086   -1.5967   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604   -0.5255   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    1.1557   -1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001    2.8013    2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    1.1049    2.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923    1.2248   -2.0979 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
  7  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
 11  4  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 14 25  1  0
M  END
Download

3D SDF for NP0000605 (L-Dopa)


  Mrv1652309032023562D          

 14 14  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 12  2  1  0  0  0  0
 10  3  1  0  0  0  0
  4  3  1  0  0  0  0
  1  5  1  0  0  0  0
  5  3  2  0  0  0  0
  2 13  1  0  0  0  0
 13  4  2  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
 11  6  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000605

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
WTDRDQBEARUVNC-LURJTMIESA-N

> <FORMULA>
C9H11NO4

> <MOLECULAR_WEIGHT>
197.1879

> <EXACT_MASS>
197.068807845

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.90987044668941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

> <JCHEM_LOGP>
-1.7921814507627933

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.686049362161093

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.650696949850563

> <JCHEM_PKA_STRONGEST_BASIC>
9.055027392905787

> <JCHEM_POLAR_SURFACE_AREA>
103.77999999999999

> <JCHEM_REFRACTIVITY>
49.07810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
levodopa

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000605 (L-Dopa)

HMDB0000181
     RDKit          3D
L-Dopa
 25 25  0  0  0  0  0  0  0  0999 V2000
   -3.2741   -1.2218    0.9174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774   -0.4157    0.3941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9128   -1.0011    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3206   -0.3257    0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719   -0.7684   -0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466   -0.1726   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6928    0.8912   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8612    1.4893   -0.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523    1.3472    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6205    2.4191    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    0.7409    1.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2205   -0.4472   -1.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0967   -1.1186   -1.6647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3048    0.2564   -1.8190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1285   -1.1606    0.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293   -2.2495    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3682    0.6171    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -2.0540    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870   -0.9902    2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086   -1.5967   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604   -0.5255   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    1.1557   -1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001    2.8013    2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    1.1049    2.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923    1.2248   -2.0979 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
  7  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
 11  4  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 14 25  1  0
M  END
Download

PDB for NP0000605 (L-Dopa)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1   12   13                                                  
CONECT    3   10    4    5                                                  
CONECT    4    3   13                                                       
CONECT    5    1    3                                                       
CONECT    6    7    8   11                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    3    8                                                       
CONECT   11    6                                                            
CONECT   12    2                                                            
CONECT   13    2    4   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for NP0000605 (L-Dopa)

COMPND    HMDB0000181
HETATM    1  N1  UNL     1      -3.274  -1.222   0.917  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.177  -0.416   0.394  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.913  -1.001   0.961  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.321  -0.326   0.549  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.972  -0.768  -0.583  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.147  -0.173  -1.034  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.693   0.891  -0.345  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.861   1.489  -0.787  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.052   1.347   0.792  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.621   2.419   1.468  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.893   0.741   1.215  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.221  -0.447  -1.080  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.097  -1.119  -1.665  1.00  0.00           O  
HETATM   14  O4  UNL     1      -1.305   0.256  -1.819  1.00  0.00           O  
HETATM   15  H1  UNL     1      -4.128  -1.161   0.305  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.029  -2.250   0.928  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.368   0.617   0.792  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.860  -2.054   0.640  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.987  -0.990   2.057  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.609  -1.597  -1.176  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.660  -0.525  -1.931  1.00  0.00           H  
HETATM   22  H8  UNL     1       4.321   1.156  -1.611  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.200   2.801   2.309  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.402   1.105   2.104  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.392   1.225  -2.098  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3   12   17
CONECT    3    4   18   19
CONECT    4    5    5   11
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8    9
CONECT    8   22
CONECT    9   10   11   11
CONECT   10   23
CONECT   11   24
CONECT   12   13   13   14
CONECT   14   25
END
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SMILES for NP0000605 (L-Dopa)

N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O
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INCHI for NP0000605 (L-Dopa)

InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
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View in JSmol
Synonyms
ValueSource
(-)-3-(3,4-Dihydroxyphenyl)-L-alanineChEBI
(-)-DopaChEBI
3,4-Dihydroxy-L-phenylalanineChEBI
3,4-DIHYDROXYPHENYLALANINEChEBI
3-Hydroxy-L-tyrosineChEBI
beta-(3,4-Dihydroxyphenyl)-L-alanineChEBI
beta-(3,4-Dihydroxyphenyl)alanineChEBI
Dihydroxy-L-phenylalanineChEBI
DoparChEBI
L-beta-(3,4-Dihydroxyphenyl)alanineChEBI
LevodopaChEBI
LevodopumChEBI
b-(3,4-Dihydroxyphenyl)-L-alanineGenerator
Β-(3,4-dihydroxyphenyl)-L-alanineGenerator
b-(3,4-Dihydroxyphenyl)alanineGenerator
Β-(3,4-dihydroxyphenyl)alanineGenerator
L-b-(3,4-Dihydroxyphenyl)alanineGenerator
L-Β-(3,4-dihydroxyphenyl)alanineGenerator
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoateHMDB
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acidHMDB
3,4-Dihydroxyphenyl-L-alanineHMDB
3-(3,4-Dihydroxyphenyl)-L-alanineHMDB
b-(3,4-Dihydroxyphenyl)-a-L-alanineHMDB
BendopaHMDB
beta-(3,4-Dihydroxyphenyl)-alpha-L-alanineHMDB
CidandopaHMDB
DihydroxyphenylalanineHMDB
DopaflexHMDB
DopaidanHMDB
DopalHMDB
DopalinaHMDB
DoparkineHMDB
DoparlHMDB
DopasolHMDB
DopastonHMDB
DopastoneHMDB
DopastralHMDB
DopicarHMDB
DoprinHMDB
EldopalHMDB
EldoparHMDB
EldopatecHMDB
EurodopaHMDB
Helfo-dopaHMDB
InsulaminaHMDB
L-(-)-DopaHMDB
L-3-(3,4-Dihydroxyphenyl)-alanineHMDB
L-4-5-DihydroxyphenylalanineHMDB
L-b-(3,4-Dihydroxyphenyl)-a-alanineHMDB
L-beta-(3,4-Dihydroxyphenyl)-alpha-alanineHMDB
L-DihydroxyphenylalanineHMDB
LaradopaHMDB
LarodopaHMDB
LedopaHMDB
LevedopaHMDB
LevopaHMDB
MaipedopaHMDB
PardaHMDB
PardopaHMDB
ProdopaHMDB
SyndopaHMDB
VeldopaHMDB
WeldopaHMDB
3 Hydroxy L tyrosineHMDB
Roche brand OF levodopaHMDB
L 3,4 DihydroxyphenylalanineHMDB
L-3,4-DihydroxyphenylalanineHMDB
Medphano brand OF levodopaHMDB
L DopaHMDB
Roberts brand OF levodopaHMDB
Chemical FormulaC9H11NO4
Average Mass197.1879 Da
Monoisotopic Mass197.06881 Da
IUPAC Name(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Namelevodopa
CAS Registry Number59-92-7
SMILES
N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
InChI KeyWTDRDQBEARUVNC-LURJTMIESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
Amanita muscariaLOTUS Database
AmaranthusFooDB
Amaranthus mangostanusKNApSAcK Database
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apis ceranaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Ascophyllum nodosumLOTUS Database
Asparagus officinalisFooDB
Astragalus hamosusLOTUS Database
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Basella rubraKNApSAcK Database
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisKNApSAcK Database
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Bombyx moriLOTUS Database
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica olereaceaKNApSAcK Database
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Celosia argenteaKNApSAcK Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaKNApSAcK Database
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crataegus monogynaLOTUS Database
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Cytisus copariusKNApSAcK Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
Gomphrena globosaKNApSAcK Database
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lophophora williamsiiKNApSAcK Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lupinus spp.KNApSAcK Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Mirabilis jalapaKNApSAcK Database
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mucuna birdwoodianaLOTUS Database
Mucuna holtoniiLOTUS Database
Mucuna priuriensKNApSAcK Database
Mucuna pruriensLOTUS Database
Mucuna sloaneiKNApSAcK Database
Mucuna spp.KNApSAcK Database
Mus musculusLOTUS Database
Musa acuminataKNApSAcK Database
Musa paradisiacaLOTUS Database
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia elatiorKNApSAcK Database
Opuntia ficus-indicaKNApSAcK Database
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaKNApSAcK Database
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumKNApSAcK Database
Plantago majorKNApSAcK Database
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca grandifloraKNApSAcK Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Rivina humilisKNApSAcK Database
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum esculentumKNApSAcK Database
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melanogenaKNApSAcK Database
Solanum melongenaFooDB
    • F. W. Knapp. Some Characteristics of Eggplant and Avocado Poiyphenolases. J. Food Science. 30(6),...
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaKNApSAcK Database
Stemonitis herbaticaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tenebrio molitorLOTUS Database
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Theobroma cacaoKNApSAcK Database
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaKNApSAcK Database
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285 °CNot Available
Boiling Point447.00 to 449.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility5 mg/mLNot Available
LogP-2.39Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility3.3 g/LALOGPS
logP-1.8ChemAxon
pKa (Strongest Acidic)1.65ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.08 m³·mol⁻¹ChemAxon
Polarizability18.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000181
DrugBank IDDB01235
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000567
KNApSAcK IDC00001357
Chemspider ID5824
KEGG Compound IDC00355
BioCyc IDL-DIHYDROXY-PHENYLALANINE
BiGG ID34719
Wikipedia LinkLevodopa
METLIN ID42
PubChem Compound6047
PDB IDNot Available
ChEBI ID15765
Good Scents IDrw1253531
References
General References
  1. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
  2. Cools R: Dopaminergic modulation of cognitive function-implications for L-DOPA treatment in Parkinson's disease. Neurosci Biobehav Rev. 2006;30(1):1-23. Epub 2005 Jun 1. [PubMed:15935475 ]
  3. de Jong AP, Kok RM, Cramers CA, Wadman SK, Haan E: A new method for the determination of L-dopa and 3-O-methyldopa in plasma and cerebrospinal fluid using gas chromatography and electron capture negative ion mass spectrometry. Clin Chim Acta. 1988 Jan 15;171(1):49-61. [PubMed:3127089 ]
  4. Dutton J, Copeland LG, Playfer JR, Roberts NB: Measuring L-dopa in plasma and urine to monitor therapy of elderly patients with Parkinson disease treated with L-dopa and a dopa decarboxylase inhibitor. Clin Chem. 1993 Apr;39(4):629-34. [PubMed:8472357 ]
  5. Mercuri NB, Bernardi G: The 'magic' of L-dopa: why is it the gold standard Parkinson's disease therapy? Trends Pharmacol Sci. 2005 Jul;26(7):341-4. [PubMed:15936832 ]
  6. Goldstein DS, Hahn SH, Holmes C, Tifft C, Harvey-White J, Milstien S, Kaufman S: Monoaminergic effects of folinic acid, L-DOPA, and 5-hydroxytryptophan in dihydropteridine reductase deficiency. J Neurochem. 1995 Jun;64(6):2810-3. [PubMed:7760062 ]
  7. Kagedal B, Pettersson A: Liquid-chromatographic determination of 5-S-L-cysteinyl-L-dopa with electrochemical detection in urine prepurified with a phenylboronate affinity gel. Clin Chem. 1983 Dec;29(12):2031-4. [PubMed:6416708 ]
  8. Dousa MK, Weinshilboum RM, Muenter MD, Offord KP, Decker PA, Tyce GM: L-DOPA biotransformation: correlations of dosage, erythrocyte catechol O-methyltransferase and platelet SULT1A3 activities with metabolic pathways in Parkinsonian patients. J Neural Transm (Vienna). 2003 Aug;110(8):899-910. [PubMed:12898345 ]
  9. Di Stefano A, Mosciatti B, Cingolani GM, Giorgioni G, Ricciutelli M, Cacciatore I, Sozio P, Claudi F: Dimeric L-dopa derivatives as potential prodrugs. Bioorg Med Chem Lett. 2001 Apr 23;11(8):1085-8. [PubMed:11327596 ]
  10. Tada K, Kudo T, Kishimoto Y: Effects of L-dopa or dopamine on human decidual prostaglandin synthesis. Acta Med Okayama. 1991 Oct;45(5):333-8. [PubMed:1755339 ]
  11. Crivellato E, Damiani D, Mallardi F: Comparison between the L-DOPA histofluorescence procedure and the indirect immunofluorescence with anti-T6 and -HLA-DR monoclonal antibodies in visualizing Langerhans cells of human epidermis. Acta Histochem. 1990;88(1):59-64. [PubMed:2113342 ]
  12. Michel H, Solere M, Granier P, Cauvet G, Bali JP, Pons F, Bellet-Hermann H: Treatment of cirrhotic hepatic encephalopathy with L-dopa. A controlled trial. Gastroenterology. 1980 Aug;79(2):207-11. [PubMed:6995221 ]
  13. Streifler M, Avrami E, Rabey JM: L-dopa and the secretion of sebum in Parkinsonian patients. Eur Neurol. 1980;19(1):43-8. [PubMed:7371653 ]
  14. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ]
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