ergotamine   Click here for help

GtoPdb Ligand ID: 149

Synonyms: Cafergot® | Ergomar®
Approved drug PDB Ligand
ergotamine is an approved drug (FDA (1960))
Compound class: Synthetic organic
Comment: Ergotamine is an ergot derived alkaloid.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 118.21
Molecular weight 581.26
XLogP 2.34
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(C1CN(C)C2C(=C1)c1cccc3c1c(C2)c[nH]3)NC1(C)OC2(N(C1=O)C(Cc1ccccc1)C(=O)N1C2CCC1)O
Isomeric SMILES O=C([C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O
InChI InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
InChI Key XCGSFFUVFURLIX-VFGNJEKYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1960))
IUPAC Name Click here for help
(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
International Nonproprietary Names Click here for help
INN number INN
391 ergotamine
Synonyms Click here for help
Cafergot® | Ergomar®
Database Links Click here for help
CAS Registry No. 113-15-5 (source: SciFinder)
ChEBI CHEBI:64318
ChEMBL Ligand CHEMBL442
DrugBank Ligand DB00696
DrugCentral Ligand 1043
GtoPdb PubChem SID 135650239
PubChem CID 8223
RCSB PDB Ligand ERM
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Wikipedia Ergotamine