dihydroergotamine   Click here for help

GtoPdb Ligand ID: 121

Synonyms: D.H.E. 45® | Migranal®
Approved drug PDB Ligand
dihydroergotamine is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Dihydroergotamine is an ergot alkaloid. It is used as a vasoconstrictor. The drug is administered as dihydroergotamine mesylate (PubChem CID 71171). The use of ergot alkaloids in the clinic has been discontinued or restricted due to their propensity to cause fibrosis.
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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 583.28
XLogP 2.29
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN1CC(CC2C1Cc1c[nH]c3c1c2ccc3)C(=O)NC1(C)OC2(N(C1=O)C(Cc1ccccc1)C(=O)N1C2CCC1)O
Isomeric SMILES CN1C[C@@H](C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O
InChI InChI=1S/C33H37N5O5/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1
InChI Key LUZRJRNZXALNLM-JGRZULCMSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1997))
IUPAC Name Click here for help
(2R,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),9,12,14-tetraene-4-carboxamide
International Nonproprietary Names Click here for help
INN number INN
2022 dihydroergotamine
Synonyms Click here for help
D.H.E. 45® | Migranal®
Database Links Click here for help
Specialist databases
GPCRdb Ligand dihydroergotamine
Other databases
CAS Registry No. 6190-39-2
ChEBI CHEBI:4562
ChEMBL Ligand CHEMBL1732
DrugBank Ligand DB00320
DrugCentral Ligand 888
GtoPdb PubChem SID 135650182
PubChem CID 10531
RCSB PDB Ligand 2GM
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UniChem Compound Search for chemical match using the InChIKey LUZRJRNZXALNLM-JGRZULCMSA-N
UniChem Connectivity Search for chemical match using the InChIKey LUZRJRNZXALNLM-JGRZULCMSA-N
Wikipedia Dihydroergotamine