reserpine   Click here for help

GtoPdb Ligand ID: 4823

Synonyms: Serpalan®
Approved drug
reserpine is an approved drug (FDA (1955))
Compound class: Synthetic organic
Comment: Reserpine irreversibly blocks the vesicular monoamine transporter (VMAT; gene symbols SLC18A1 and SLC18A2), to bring about depletion of monoamine neurotransmitters at synapses.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 117.78
Molecular weight 608.27
XLogP 3.63
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1ccc2c(c1)[nH]c1c2CCN2C1CC1C(C2)CC(C(C1C(=O)OC)OC)OC(=O)c1cc(OC)c(c(c1)OC)OC
Isomeric SMILES COc1ccc2c(c1)[nH]c1c2CCN2[C@@H]1C[C@H]1[C@@H](C2)C[C@H]([C@@H]([C@H]1C(=O)OC)OC)OC(=O)c1cc(OC)c(c(c1)OC)OC
InChI InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
InChI Key QEVHRUUCFGRFIF-MDEJGZGSSA-N
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Vesicular monoamine transporter 2 Primary target of this compound Hs Inhibitor Inhibition 7.9 pKi - 1
pKi 7.9 (Ki 1.2x10-8 M) [1]
Vesicular monoamine transporter 1 Hs Inhibitor Inhibition 7.4 pKi - 1
pKi 7.4 (Ki 3.4x10-8 M) [1]