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Also known as: 5-hydroxytryptamine, 50-67-9, 3-(2-aminoethyl)-1h-indol-5-ol, Enteramine, Thrombotonin, 5-ht

Molecular Formula

C₁₀H₁₂N₂O

Molecular Weight

176.21 g/mol

InChI Key

QZAYGJVTTNCVMB-UHFFFAOYSA-N

FDA UNII

333DO1RDJY

A biochemical messenger and regulator, synthesized from the essential amino acid L-TRYPTOPHAN. In humans it is found primarily in the central nervous system, gastrointestinal tract, and blood platelets. Serotonin mediates several important physiological functions including neurotransmission, gastrointestinal motility, hemostasis, and cardiovascular integrity. Multiple receptor families (RECEPTORS, SEROTONIN) explain the broad physiological actions and distribution of this biochemical mediator.

1 2D Structure

Serotonin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(2-aminoethyl)-1H-indol-5-ol

2.1.2 InChI

InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2

2.1.3 InChI Key

QZAYGJVTTNCVMB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC2=C(C=C1O)C(=CN2)CCN

2.2 Other Identifiers

2.2.1 UNII

333DO1RDJY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(2-aminoethyl)-1h-indol-5-ol

2. 5 Hydroxytryptamine

3. 5-ht

4. 5-hydroxytryptamine

5. Enteramine

6. Hippophaine

7. Hydroxytryptamine

2.3.2 Depositor-Supplied Synonyms

1. 5-hydroxytryptamine

2. 50-67-9

3. 3-(2-aminoethyl)-1h-indol-5-ol

4. Enteramine

5. Thrombotonin

6. 5-ht

7. Thrombocytin

8. Antemovis

9. Serotonine

10. Ds Substance

11. Hippophain

12. Antemoqua

13. Substance Ds

14. Substanz Ds

15. 3-(2-aminoethyl)indol-5-ol

16. 1h-indol-5-ol, 3-(2-aminoethyl)-

17. 5-hta

18. Tryptamine, 5-hydroxy-

19. Enteramin

20. Indol-5-ol, 3-(2-aminoethyl)-

21. 3-(beta-aminoethyl)-5-hydroxyindole

22. 5-hydroxy-3-(beta-aminoethyl)indole

23. 3-(2-amino-ethyl)-1h-indol-5-ol

24. 333do1rdjy

25. Chebi:28790

26. 3-(.beta.-aminoethyl)-5-hydroxyindole

27. Hippophaine

28. [3h]-5-ht

29. Einecs 200-058-9

30. Unii-333do1rdjy

31. Brn 0143524

32. 5-hydroxytryptamin

33. 5-hydroxytriptamine

34. 5-hydroxyltryptamine

35. 5-hydroxy-tryptamine

36. 1h-indol-5-ol,3-(2-aminoethyl)-

37. 5-hydroxyl Tryptamine

38. Gtpl5

39. Serotonin [mi]

40. Chembl39

41. Prestwick0_000481

42. Prestwick1_000481

43. Prestwick2_000481

44. Prestwick3_000481

45. Lopac-h-9523

46. 5-hydroxytryptamine;5-ht

47. Biomol-nt_000083

48. Bmse000757

49. Serotonin [mart.]

50. Schembl1495

51. Serotonin [who-dd]

52. Lopac0_000607

53. Oprea1_712368

54. Bspbio_000341

55. Bspbio_001112

56. Kbiogr_000452

57. Kbiogr_002472

58. Kbioss_000452

59. Kbioss_002479

60. 5-22-12-00016 (beilstein Handbook Reference)

61. Serotonin, Analytical Standard

62. Spbio_002262

63. 5-hydroxytryptamine, Free Base

64. Bpbio1_000377

65. Bpbio1_001079

66. Dtxsid8075330

67. Bcbcmap01_000198

68. Bdbm10755

69. Kbio2_000452

70. Kbio2_002472

71. Kbio2_003020

72. Kbio2_005040

73. Kbio2_005588

74. Kbio2_007608

75. Kbio3_000843

76. Kbio3_000844

77. Kbio3_002950

78. Zinc57058

79. Cmap_000059

80. 3-(b-aminoethyl)-5-hydroxyindole

81. 5-hydroxy-3-(b-aminoethyl)indole

82. Bio1_000450

83. Bio1_000939

84. Bio1_001428

85. Bio2_000396

86. Bio2_000876

87. Hms1362h13

88. Hms1792h13

89. Hms1990h13

90. Hms3403h13

91. 3-(2-aminoethyl)-1h-indol-5-o

92. Albb-006183

93. Mfcd00055054

94. Pdsp1_001512

95. Pdsp2_001496

96. Stk503758

97. Akos001484724

98. 3-(2-aminoethyl)-1h-indol-5-ol #

99. Ccg-204696

100. Db08839

101. Sdccgsbi-0050589.p002

102. 5-hydroxy-3-(.beta.-aminoethyl)indole

103. Idi1_002151

104. Smp1_000272

105. 5-hydroxy Tryptamine Creatinine Disulfate

106. Ncgc00015525-01

107. Ncgc00015525-02

108. Ncgc00015525-03

109. Ncgc00015525-04

110. Ncgc00015525-05

111. Ncgc00015525-06

112. Ncgc00015525-07

113. Ncgc00015525-08

114. Ncgc00015525-09

115. Ncgc00015525-19

116. Ncgc00142449-01

117. Ncgc00142449-02

118. Ncgc00142449-03

119. Ncgc00142449-04

120. Ncgc00142449-05

121. As-75772

122. Cas-153-98-0

123. Db-051820

124. Ft-0631212

125. 14c-5-hydroxy Tryptamine Creatinine Disulfate

126. C00780

127. H-8000

128. A828245

129. L000078

130. Q167934

131. 6f7fd5b4-a558-45f0-a20a-2d068a3efe6a

132. 2-imino-1-methylimidazolidin-4-one; 3-(2-aminoethyl)-1h-indol-5-ol; Bis(sulfuric Acid)

133. 1094000-36-8

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₂N₂O
Molecular Weight	176.21 g/mol
XLogP3	0.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	176.094963011 g/mol
Monoisotopic Mass	176.094963011 g/mol
Topological Polar Surface Area	62 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	174
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Serotonin Receptor Agonists

Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS. (See all compounds classified as Serotonin Receptor Agonists.)

4.2 Metabolism/Metabolites

Serotonin has known human metabolites that include (2S,3S,4S,5R)-6-[[3-(2-Aminoethyl)-1H-indol-5-yl]oxy]-3,4,5-trihydroxy-2-oxanecarboxylic acid and 3-Ethyl-1H-indol-5-ol.

Serotonin is a known human metabolite of 5-methoxytryptamine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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