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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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View more information in the IUPHAR Pharmacology Education Project: diamorphine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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
Search Google for chemicals with the same backbone GVGLGOZIDCSQPN
UniChem Compound Search for chemical match using the InChIKey GVGLGOZIDCSQPN-PVHGPHFFSA-N
UniChem Connectivity Search for chemical match using the InChIKey GVGLGOZIDCSQPN-PVHGPHFFSA-N