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
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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
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
Search Google for chemical match using the InChIKey GVGLGOZIDCSQPN-PVHGPHFFSA-N
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UniChem Compound Search for chemical match using the InChIKey GVGLGOZIDCSQPN-PVHGPHFFSA-N
UniChem Connectivity Search for chemical match using the InChIKey GVGLGOZIDCSQPN-PVHGPHFFSA-N