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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
References
1. Erickson JD, Schafer MK, Bonner TI, Eiden LE, Weihe E. (1996)
Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter.
Proc Natl Acad Sci USA, 93 (10): 5166-71. [PMID:8643547]