5-hydroxytryptamine   Click here for help

GtoPdb Ligand ID: 5

Abbreviated name: 5-HT
Synonyms: serotonin
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 62.04
Molecular weight 176.09
XLogP 1
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NCCc1c[nH]c2c1cc(O)cc2
Isomeric SMILES NCCc1c[nH]c2c1cc(O)cc2
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
InChI Key QZAYGJVTTNCVMB-UHFFFAOYSA-N
Natural/Endogenous Targets
Target
5-HT3A
5-HT3B
5-HT3C
5-HT3D
5-HT3E
5-HT1A receptor
5-HT1B receptor
5-HT1D receptor
5-ht1e receptor
5-HT1F receptor
5-HT2A receptor
5-HT2B receptor
5-HT2C receptor
5-HT3A
5-HT3AB
5-HT4 receptor
5-HT5A receptor
5-ht5b receptor
5-HT6 receptor
5-HT7 receptor
D1 receptor
D5 receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
L-Aromatic amino-acid decarboxylase
Monoamine oxidase A
Monoamine oxidase B
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Vesicular monoamine transporter 2 29
Organic cation transporter 1
Organic cation transporter 3 86
Plasma membrane monoamine transporter 28,82
Vesicular monoamine transporter 1 29
SERT
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT2A receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.9 pKd - 75
pKd 8.9 [75]
5-HT4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.4 – 8.8 pKd - 10
pKd 8.4 – 8.8 [10]
5-HT1F receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.0 pKd - 3
pKd 8.0 [3]
5-HT1B receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.5 – 8.4 pKd - 66,84
pKd 7.5 – 8.4 [66,84]
5-HT6 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.9 pKd - 13
pKd 7.9 [13]
5-HT4 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.7 pKd - 2
pKd 7.7 [2]
5-HT1A receptor Ligand is endogenous in the given species Hs Agonist Full agonist 9.1 – 9.7 pKi - 41,61-65
pKi 9.1 – 9.7 [41,61-65]
5-HT7 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 8.7 – 9.2 pKi - 71,74
pKi 8.7 – 9.2 [71,74]
5-HT7 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.1 – 9.6 pKi - 7,35,39,45,78
pKi 8.1 – 9.6 [7,35,39,45,78]
5-HT1D receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.0 – 9.0 pKi - 22,34,48,62,72,83-84
pKi 8.0 – 9.0 [22,34,48,62,72,83-84]
5-HT7 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.3 pKi - 67
pKi 8.3 [67]
5-HT1B receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.4 – 9.0 pKi - 22,60,62,72,83-84
pKi 7.4 – 9.0 [22,60,62,72,83-84]
5-HT2B receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.9 – 8.4 pKi - 8,43,46,52,70
pKi 7.9 – 8.4 [8,43,46,52,70]
5-HT1B receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.1 pKi - 50
pKi 8.1 [50]
5-ht1e receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.0 – 8.2 pKi - 3,6,25,53
pKi 8.0 – 8.2 [3,6,25,53]
5-HT2B receptor Ligand is endogenous in the given species Rn Agonist Full agonist 8.0 pKi - 80
pKi 8.0 [80]
5-HT1F receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.7 – 8.0 pKi - 1,3,81
pKi 7.7 – 8.0 [1,3,81]
5-HT2C receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.8 – 8.6 pKi - 26,31,42-43,52
pKi 6.8 – 8.6 [26,31,42-43,52]
5-HT4 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.7 – 8.2 pKi - 2,16,32
pKi 6.7 – 8.2 [2,16,32]
5-HT2C receptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.7 – 7.9 pKi - 36,70
pKi 6.7 – 7.9 [36,70]
5-HT6 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.6 – 7.9 pKi - 13-15,59
pKi 6.6 – 7.9 [13-15,59]
5-HT2A receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.0 – 8.4 pKi - 4,18,40,43,52,75
pKi 6.0 – 8.4 [4,18,40,43,52,75]
5-HT4 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.2 pKi - 20
pKi 7.2 [20]
5-HT6 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.8 – 7.5 pKi - 12,15,44
pKi 6.8 – 7.5 [12,15,44]
5-HT5A receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.7 – 6.9 pKi - 33,68
pKi 6.7 – 6.9 [33,68]
5-HT5A receptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.6 pKi - 30
pKi 6.6 [30]
5-HT4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.9 – 7.0 pKi - 5,8,10-11,19,55-57,69,79
pKi 5.9 – 7.0 [5,8,10-11,19,55-57,69,79]
5-HT5A receptor Ligand is endogenous in the given species Mm Agonist Full agonist 6.0 – 6.6 pKi - 33,51,85
pKi 6.0 – 6.6 [33,51,85]
5-HT2A receptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.0 – 6.5 pKi - 27,70,73
pKi 6.0 – 6.5 [27,70,73]
D5 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.5 pKi - 77
pKi 5.5 [77]
D1 receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 5.0 pKi - 77
pKi 5.0 [77]
5-HT1F receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.2 pIC50 - 49
pIC50 7.2 [49]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT3A Ligand is endogenous in the given species Hs Agonist Agonist 6.5 – 6.9 pKi - 17,37-38,47
pKi 6.5 – 6.9 [17,37-38,47]
5-HT3AB Ligand is endogenous in the given species Hs Agonist Agonist 6.0 pKi - 17
pKi 6.0 [17]
5-HT3A Ligand is endogenous in the given species Hs Agonist Agonist 5.5 – 6.4 pEC50 - 9,21,23-24,47,58,76
pEC50 5.5 – 6.4 [9,21,23-24,47,58,76]
5-HT3AB Ligand is endogenous in the given species Hs Agonist Agonist 4.8 – 5.8 pEC50 - 21,23-24,76
pEC50 4.8 – 5.8 [21,23-24,76]
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Proton-coupled Amino acid Transporter 1 Hs Inhibitor Inhibition 2.2 pKi - 54
pKi 2.2 (Ki 5.7x10-3 M) [54]
Ligand mentioned in the following text fields