(-)-adrenaline   Click here for help

GtoPdb Ligand ID: 479

Synonyms: adrenalin | Auvi-Q® | Epipen® | l-adrenaline | L-epinephrine | levoepinephrine
Approved drug PDB Ligand Immunopharmacology Ligand
(-)-adrenaline is an approved drug (FDA (no history prior to 1951))
Comment: Agonist at alpha and beta adrenoceptors. In addition to being assigned the INN epinephrine in its own right, (-)-adrenaline is also one of the enantiomers found in the INN-assigned compound (±)-adrenaline.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 72.72
Molecular weight 183.09
XLogP 0.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNCC(c1ccc(c(c1)O)O)O
Isomeric SMILES CNC[C@@H](c1ccc(c(c1)O)O)O
InChI InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
InChI Key UCTWMZQNUQWSLP-VIFPVBQESA-N
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (no history prior to 1951))
IUPAC Name Click here for help
4-[(1R)-1-hydroxy-2-methylaminoethyl]benzene-1,2-diol
International Nonproprietary Names Click here for help
INN number INN
2142 epinephrine
4553 racepinefrine
Synonyms Click here for help
adrenalin | Auvi-Q® | Epipen® | l-adrenaline | L-epinephrine | levoepinephrine
Database Links Click here for help
BindingDB Ligand 50029050
CAS Registry No. 51-43-4
ChEBI CHEBI:28918
ChEMBL Ligand CHEMBL679
DrugBank Ligand DB00668
DrugCentral Ligand 1028
GtoPdb PubChem SID 135651430
Immunopaedia Search epinephrine
PubChem CID 5816
RCSB PDB Ligand ALE
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Search PubMed clinical trials racepinefrine
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Search PubMed titles/abstracts racepinefrine
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SynPHARM 1862 (in complex with β2-adrenoceptor)
Wikipedia Epinephrine