(-)-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))
Compound class: Metabolite
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
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
Specialist databases
GPCRdb Ligand (-)-adrenaline
Other databases
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
Search Google for chemical match using the InChIKey UCTWMZQNUQWSLP-VIFPVBQESA-N
Search Google for chemicals with the same backbone UCTWMZQNUQWSLP
Search PubMed clinical trials racepinefrine
Search PubMed titles racepinefrine
Search PubMed titles/abstracts racepinefrine
SynPHARM 1862 (in complex with β2-adrenoceptor)
UniChem Compound Search for chemical match using the InChIKey UCTWMZQNUQWSLP-VIFPVBQESA-N
UniChem Connectivity Search for chemical match using the InChIKey UCTWMZQNUQWSLP-VIFPVBQESA-N
Wikipedia Epinephrine