yohimbine   Click here for help

GtoPdb Ligand ID: 102

Synonyms: Actibine® | corynine | quebrachin | yohimbin
Approved drug
yohimbine is an approved drug (FDA (no date available))
Comment: Yohimbine exerts actions on many receptors of the dopamine, serotonin and adrenergic families, with highest activity as an antagonist of α2-adrenoceptors.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 65.56
Molecular weight 354.19
XLogP 2.72
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COC(=O)C1C(O)CCC2C1CC1N(C2)CCc2c1[nH]c1c2cccc1
Isomeric SMILES COC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1
InChI InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
InChI Key BLGXFZZNTVWLAY-SCYLSFHTSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
α2C-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 8.5 – 9.5 pKi - 4-5,14
pKi 8.5 – 9.5 [4-5,14]
α2A-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 8.4 – 9.2 pKi - 4-5,14
pKi 8.4 – 9.2 [4-5,14]
α2B-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 7.9 – 8.9 pKi - 4-5,14
pKi 7.9 – 8.9 [4-5,14]
5-HT1B receptor Mm Antagonist Antagonist 8.3 pKi - 10
pKi 8.3 [10]
5-HT2B receptor Hs Antagonist Antagonist 7.4 – 7.9 pKi - 3,7,16
pKi 7.4 – 7.9 [3,7,16]
5-HT1D receptor Hs Antagonist Antagonist 7.2 – 7.7 pKi - 6,8,12,17
pKi 7.2 – 7.7 [6,8,12,17]
5-HT1A receptor Hs Antagonist Antagonist 7.3 pKi - 12
pKi 7.3 [12]
5-HT2B receptor Rn Antagonist Antagonist 7.3 pKi - 15
pKi 7.3 [15]
5-HT1B receptor Hs Antagonist Antagonist 6.8 – 7.6 pKi - 12,17
pKi 6.8 – 7.6 [12,17]
5-HT1F receptor Hs Antagonist Antagonist 7.0 pKi - 1
pKi 7.0 [1]
5-ht1e receptor Hs Antagonist Antagonist 5.9 pKi - 1
pKi 5.9 [1]
5-HT7 receptor Hs Antagonist Antagonist 5.6 pKi - 2
pKi 5.6 [2]
5-HT5A receptor Mm Antagonist Antagonist 4.9 – 6.0 pKi - 11,18
pKi 4.9 – 6.0 [11,18]
5-HT5A receptor Hs Antagonist Antagonist 5.3 pKi - 13
pKi 5.3 [13]
5-HT1F receptor Rn Antagonist Antagonist 6.2 pIC50 - 9
pIC50 6.2 [9]
Ligand mentioned in the following text fields