ergometrine   Click here for help

GtoPdb Ligand ID: 148

Synonyms: ergonovine | Ergotrate® | Methergine®
Approved drug
ergometrine is an approved drug
Compound class: Synthetic organic
Comment: Ergometrine is an ergot alkaloid which causes contraction of uterine and vascular smooth muscle cells acting through a variety of GPCRs (such as adrenoceptors, dopamine receptors, and 5-HT receptors).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 68.36
Molecular weight 325.18
XLogP 1.18
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC(NC(=O)C1CN(C)C2C(=C1)c1cccc3c1c(C2)c[nH]3)C
Isomeric SMILES OC[C@@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)C
InChI InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1
InChI Key WVVSZNPYNCNODU-XTQGRXLLSA-N
References
1. Bai F, Yin T, Johnstone EM, Su C, Varga G, Little SP, Nelson DL. (2004)
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
Eur. J. Pharmacol., 484 (2-3): 127-39. [PMID:14744596]
2. Johnson MP, Loncharich RJ, Baez M, Nelson DL. (1994)
Species variations in transmembrane region V of the 5-hydroxytryptamine type 2A receptor alter the structure-activity relationship of certain ergolines and tryptamines.
Mol. Pharmacol., 45 (2): 277-86. [PMID:8114677]