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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL465
CHEMBL465
Compound Name DRONABINOL
ChEMBL Synonyms Marinol | Dronabinol | delta-9-THC | delta-9-Tetrahydrocannabinol
Max Phase 4 (Approved)
Trade Names Marinol | Dronabinol
Molecular Formula C21H30O2

Additional synonyms for CHEMBL465 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCCc1cc(O)c2[C@@H]3C=C(C)CC[C@H]3C(C)(C)Oc2c1
Standard InChI InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10- ...
Download InChI
Standard InChI Key CYQFCXCEBYINGO-IAGOWNOFSA-N

Mechanism of Action

Mechanism of Action ChEMBL Target References
Cannabinoid CB1 receptor agonist Cannabinoid CB1 receptor DailyMed PubMed

Molecule Features

CHEMBL465 compound icon
Drug Type:Natural Product Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

Structural Alerts

There are 2 structural alerts for CHEMBL465. To view alerts please click here.

Alternate Forms of Compound in ChEMBL


CHEMBL465

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL465. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL5160 Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus 1.000
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 0.896
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 0.494
CHEMBL3892 Sphingosine 1-phosphate receptor Edg-3 Homo sapiens 0.207



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL5160 Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 0.904
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 0.892
CHEMBL3318 Tyrosinase Agaricus bisporus 0.429
CHEMBL4666 Steroidogenic factor 1 Homo sapiens 0.239
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.239

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
314.5 314.2246 6.11 4 29.46 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 1 2 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.81 - 6.84 6.84 1 23 0.54

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A04 - ANTIEMETICS AND ANTINAUSEANTS
A04A - ANTIEMETICS AND ANTINAUSEANTS
A04AD - Other antiemetics
A04AD10 - dronabinol

ChemSpider ChemSpider:CYQFCXCEBYINGO-IAGOWNOFSA-N
DailyMed dronabinol
PubChem SID: 144206169
Wikipedia Tetrahydrocannabinol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL465



ACToR 1363-19-5 6465-30-1 1972-08-3 308064-99-5
BindinDB 50007391
ChEBI 66964
DrugBank DB00470
eMolecules 27524156 594744
FDA SRS 7J8897W37S
Guide to Pharmacology 2424
Human Metabolome Database HMDB14613
IBM Patent System 70DF85191FFCEF8AD9F57A6A76728800
IBM Patents WO2001066089A2 WO2010105672A1 US20020187514 EP2166846A1 WO2008156757A1 US20040138315 WO2010025272A1 WO2007022535A2 EP2231159A1 US20080206193 US20050089495 US7638549 WO2009051712A1 US20090202549 WO2007089907A2 WO2009092770A1 US20070020630 WO2004096131A2 WO2005063729A1 US20030068276 WO2010115426A1 WO2001011048A2 EP2139508A2 US20090117096 EP1594856A1 US5219747 US20050182351 WO2007147746A1 US20090054376 EP1023466A2 EP1307197B1 US20030008886 EP1653939A2 WO2002097038A2 US7134999 US4380542 US20060167084 US20090142343 WO2008039489A2 US20100305208 EP2102212A1 US20080138336 EP1910564A1 EP1740161A2 WO2010065936A1 US20080076921 EP1829876A1 US5256575 US20060100212 US20060135594 US20060079557 EP1394154A1 EP1868999B1 WO2004064826A1 WO2009143454A2 WO2005102296A2 EP0271204A2 EP2018863A1 US20050115832 US20090232907 WO2006022714A1 EP1976884A2 US20060160762 EP1749819A1 EP0585310A1 EP1620411B1 US20100286048 EP1778172A1 US6013646 US6548518 US20030022390 EP2125758A1 US20060252027 WO2009001092A1 EP1992348A1 WO1996031496A1 US7829581 EP1301524A1 WO1997001097A1 US5445944 WO2008066691A2 US20100055099 WO2006026260A1 EP1648878A1 US7825148 WO2010093434A1 WO2007092436A2 WO2005035500A2 US6280743 US20060247320 US5989535 US5710256 US7423144 US20020086820 WO2010111711A2 US4310668 US20040106975 US20090253727 EP1578841A2 US20060235285
KEGG Ligand C06972
Nikkaji J882F
PDBe TCI
PubChem 16078
PubChem: Drugs of the Future 12013925
PubChem: Thomson Pharma 14899056 14776764
SureChEMBL SCHEMBL4609
ZINC ZINC01530625

UniChem REST Service Call: https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/CYQFCXCEBYINGO-IAGOWNOFSA-N spacer
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