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Chemistry

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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

Dl-Dopa
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 Weight 197.19 g/mol
Molecular Formula C9H11NO4
XLogP3-2.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass197.06880783 g/mol
Monoisotopic Mass197.06880783 g/mol
Topological Polar Surface Area104 Ų
Heavy Atom Count14
Formal Charge0
Complexity209
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.)


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