Dl-Dopa

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Also known as: 63-84-3, 3,4-dihydroxy-dl-phenylalanine, 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid, 3-(3,4-dihydroxyphenyl)-dl-alanine, 3-hydroxytyrosine, Dihydroxyphenylalanine

Molecular Formula

C₉H₁₁NO₄

Molecular Weight

197.19 g/mol

InChI Key

WTDRDQBEARUVNC-UHFFFAOYSA-N

FDA UNII

QI9C343R60

A beta-hydroxylated derivative of phenylalanine. The D-form of dihydroxyphenylalanine has less physiologic activity than the L-form and is commonly used experimentally to determine whether the pharmacological effects of LEVODOPA are stereospecific.

1 2D Structure

Dl-Dopa

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

2.1.2 InChI

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)

2.1.3 InChI Key

WTDRDQBEARUVNC-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1CC(C(=O)O)N)O)O

2.2 Other Identifiers

2.2.1 UNII

QI9C343R60

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3 Hydroxy Dl Tyrosine

2. 3,4 Dihydroxyphenylalanine

3. 3,4-dihydroxyphenylalanine

4. 3-hydroxy-dl-tyrosine

5. Beta Hydroxytyrosine

6. Beta-hydroxytyrosine

7. Dihydroxyphenylalanine

8. Dihydroxyphenylalanine Hydrochloride, (2:1)

9. Dopa

2.3.2 Depositor-Supplied Synonyms

1. 63-84-3

2. 3,4-dihydroxy-dl-phenylalanine

3. 2-amino-3-(3,4-dihydroxyphenyl)propanoic Acid

4. 3-(3,4-dihydroxyphenyl)-dl-alanine

5. 3-hydroxytyrosine

6. Dihydroxyphenylalanine

7. Dl-dioxyphenylalanine

8. Dl-dihydroxyphenylalanine

9. Dopa

10. Dl-tyrosine, 3-hydroxy-

11. 3-hydroxy-dl-tyrosine

12. Dl-3,4-dopa

13. Dl-3-hydroxytyrosine

14. (r,s)-dopa

15. (+-)-dopa

16. Dl-beta-(3,4-dihydroxyphenyl)alanine

17. 3',4'-dihydroxyphenylalanine

18. (+-)-3-(3,4-dihydroxyphenyl)alanine

19. 587-45-1

20. D-b-3,4-dihydroxyphenylalanine

21. Chebi:49168

22. Qi9c343r60

23. 2-amino-3-(3,4-dihydroxy-phenyl)-propionic Acid

24. Alanine, 3-(3,4-dihydroxyphenyl)-, Dl-

25. Nsc-16940

26. Tyrosine, 3-hydroxy-

27. D-3-(3,4-dihydroxyphenyl)alanine

28. D-tyrosine, 3-hydroxy-

29. Dl-3,4-dihydroxyphenylalanine

30. Wln: Qvyz1r Cq Dq

31. Einecs 200-566-0

32. Nsc 16940

33. Unii-qi9c343r60

34. Ai3-23874

35. Mfcd00002598

36. Nsc-118368

37. Beta-(3,4-dihydroxyphenyl)-alpha-alanine

38. Alanine, 3-(3,4-dihydroxyphenyl)-, D-

39. D-3-hydroxytyrosine

40. Mfcd00063060

41. Dopa Dl-form

42. Dopa, Dl-

43. Dopa Dl-form [mi]

44. Schembl24360

45. Alpha-amino-hydrocaffeic Acid

46. (.+-.)-dopa

47. 3,4-dihydroxyphenylalanine #

48. Dl-4,5-dihydroxyphenylalanine

49. Bdbm4377

50. Chembl351042

51. Dtxsid8020549

52. Alanine,4-dihydroxyphenyl)-, D-

53. Dl-3',4'-dihydroxyphenylalanine

54. 3(3,4-dihydroxyphenyl)dl-alanine

55. Alanine,4-dihydroxyphenyl)-, Dl-

56. Bcp25747

57. Nsc16940

58. B-(3,4-dihydroxyphenyl)-a-alanine

59. Dl-b-(3,4-dihydroxyphenyl)alanine

60. 3-(3,4-dihydroxyphenyl)-d-alanine

61. Bbl010087

62. Nsc118368

63. Stk801445

64. (.+-.)-3,4-dihydroxyphenylalanine

65. Akos001132704

66. Akos016843592

67. 3,4-dihydroxy-dl-phenylalanine, 97%

68. Gs-6861

69. Pb43103

70. A-amino-3,4-dihydroxy-benzenepropanoate

71. L-dopa; 3,4-dihydroxy-l-phenylalanine

72. Ncgc00015384-02

73. Ncgc00015384-03

74. Ncgc00095195-01

75. Ncgc00095195-02

76. (+/-) 3-(3,4-dihydroxyphenyl)alanine

77. As-81574

78. Bp-12841

79. Dl-.beta.-(3,4-dihydroxyphenyl)alanine

80. Sy010977

81. (.+-.)-3-(3,4-dihydroxyphenyl)alanine

82. Dl-alanine, 3-(3,4-dihydroxy-phenyl)-

83. (+/-)-3,4-dihydroxyphenylalanine

84. 2-amino-3-(3,4-dihydroxyphenyl)propanoate

85. Alpha-amino-3,4-dihydroxy-benzenepropanoate

86. Db-053498

87. Hy-113404

88. A-amino-3,4-dihydroxy-benzenepropanoic Acid

89. Cs-0059346

90. D0599

91. D9503

92. Dl-beta-(3,4-dihydroxyphenyl)-alpha-alanine

93. Ft-0603250

94. Ft-0650636

95. Ft-0667771

96. Ft-0695064

97. Ft-0775213

98. S6083

99. Beta-(3,4-dihydroxyphenyl)-dl-alpha-alanine

100. Alpha-amino-3,4-dihydroxy-benzenepropanoic Acid

101. Alpha-amino-3,4-dihydroxybenzenepropanoic Acid

102. H11952

103. .beta.-(3,4-dihydroxyphenyl)-dl-.alpha.-alanine

104. A834552

105. L001274

106. (2-pyrrolidin-3-yl-ethyl)-carbamic Acid Benzyl Ester

107. Q27121510

108. Z94598614

109. Dd916368-6635-446f-af55-7b416fd65026

110. Im3

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₁NO₄
Molecular Weight	197.19 g/mol
XLogP3	-2.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	197.06880783 g/mol
Monoisotopic Mass	197.06880783 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	209
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Dopamine Agents

Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons. (See all compounds classified as Dopamine Agents.)