bufotenine   Click here for help

GtoPdb Ligand ID: 144

Synonyms: 5-OH-DMT | dimethylserotonin | DM5-HT | N,N-dimethyl-5-HT | N,N-dimethylserotonin
Compound class: Synthetic organic
Comment: Bufotenin is a serotonin-like bioactive toxin found in the skin of certain poisonous toads, mushrooms and tree seeds that has hallucinogenic effects.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 39.26
Molecular weight 204.13
XLogP 1.63
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN(CCc1c[nH]c2c1cc(O)cc2)C
Isomeric SMILES CN(CCc1c[nH]c2c1cc(O)cc2)C
InChI InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
InChI Key VTTONGPRPXSUTJ-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT1D receptor Hs Antagonist Antagonist 7.7 – 8.0 pKi - 3
pKi 7.7 – 8.0 [3]
5-HT6 receptor Rn Antagonist Antagonist 7.0 – 8.4 pKi - 2
pKi 7.0 – 8.4 [2]
5-HT7 receptor Mm Agonist Full agonist 7.0 pKi - 5
pKi 7.0 [5]
5-HT2A receptor Hs Antagonist Antagonist 6.8 pKi - 1
pKi 6.8 [1]
5-HT5A receptor Mm Antagonist Antagonist 5.3 – 6.0 pKi - 4,6
pKi 5.3 – 6.0 [4,6]