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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1955))
IUPAC Name Click here for help
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
International Nonproprietary Names Click here for help
INN number INN
282 reserpine
Synonyms Click here for help
Serpalan®
Database Links Click here for help
CAS Registry No. 50-55-5 (source: Scifinder)
ChEMBL Ligand CHEMBL772
DrugBank Ligand DB00206
DrugCentral Ligand 2370
GtoPdb PubChem SID 178101525
PubChem CID 5770
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Wikipedia Reserpine

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Tocris
Reserpine
Cat. No. 2742