artenimol   Click here for help

GtoPdb Ligand ID: 9957

Synonyms: DHA | dihydroartemisinin | GNF-Pf-5634
Approved drug Antimalarial Ligand
artenimol is an approved drug (EMA (2011) in combination with piperaquine)
Compound class: Natural product or derivative
Comment: Artenimol is the active metabolite of artemisinin and all artemisinin-derived antimalarial compounds.
We show one representation of artenimol here. As with other natural products, there are alternative chemical structures due to the complex stereochemistry.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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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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 CDK toolkit. 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 5
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 57.15
Molecular weight 284.16
XLogP 2.81
No. Lipinski's rules broken 0
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.

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Canonical SMILES OC1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
Isomeric SMILES O[C@H]1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
InChI InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
InChI Key BJDCWCLMFKKGEE-ISOSDAIHSA-N
Classification Click here for help
Compound class Natural product or derivative
Ligand families/groups Antimalarial ligands
Approved drug? Yes (EMA (2011) in combination with piperaquine)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(3r,5as,6r,8as,9r,10s,12r,12ar)-decahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano[4,3-j][1,2]benzodioxepin-10-ol
International Nonproprietary Names Click here for help
INN number INN
7777 artenimol
Synonyms Click here for help
DHA | dihydroartemisinin | GNF-Pf-5634
Database Links Click here for help
CAS Registry No. 71939-50-9 (source: Scifider)
DrugCentral Ligand 4194
GtoPdb PubChem SID 374883844
PubChem CID 3000518
Search Google for chemical match using the InChIKey BJDCWCLMFKKGEE-ISOSDAIHSA-N
Search Google for chemicals with the same backbone BJDCWCLMFKKGEE
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UniChem Compound Search for chemical match using the InChIKey BJDCWCLMFKKGEE-ISOSDAIHSA-N
UniChem Connectivity Search for chemical match using the InChIKey BJDCWCLMFKKGEE-ISOSDAIHSA-N