diamorphine   Click here for help

GtoPdb Ligand ID: 9082

Synonyms: acetomorphine | diacetylmorphine | heroin
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Diamorphine (heroin) is a morphine derivative. It acts as a potent opioid receptor agonist after deacetylation to 6-acetylmorphine and subsequently to morphine [2].
Internationally, heroin is a controlled narcotic drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 65.07
Molecular weight 369.16
XLogP 1.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(=O)OC1C=CC2C34C1Oc1c4c(CC2N(CC3)C)ccc1OC(=O)C
Isomeric SMILES CC(=O)O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC(=O)C
InChI InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
InChI Key GVGLGOZIDCSQPN-PVHGPHFFSA-N
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form morphine
IUPAC Name Click here for help
[(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl] acetate
Synonyms Click here for help
acetomorphine | diacetylmorphine | heroin
Database Links Click here for help
ChEMBL Ligand CHEMBL459324
DrugBank Ligand DB01452
DrugCentral Ligand 4412
GtoPdb PubChem SID 315661167
PubChem CID 5462328
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