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    Chemistry

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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
    Serotonin
    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 Weight 176.21 g/mol
    Molecular Formula C10H12N2O
    XLogP30.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count2
    Exact Mass176.094963011 g/mol
    Monoisotopic Mass176.094963011 g/mol
    Topological Polar Surface Area62 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity174
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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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    09-Sep-2021
    09-Sep-2021
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