Δ9-tetrahydrocannabinol   Click here for help

GtoPdb Ligand ID: 2424

Abbreviated name: THC
Synonyms: Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Approved drug PDB Ligand
Δ9-tetrahydrocannabinol is an approved drug (FDA (1985))
Compound class: Natural product
Comment: Δ9-tetrahydrocannabinol is the principle active ingredient derived from the cannabis plant (Cannabis sativa). Dronabinol is the INN for the pure, synthetically produced (-)-trans9-tetrahydrocannabinol isomer of tetrahydrocannabinol (shown here).
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View more information in the IUPHAR Pharmacology Education Project: delta-9-tetrahydrocannabinol

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 0
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 29.46
Molecular weight 314.22
XLogP 6.47
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCc1cc(O)c2c(c1)OC(C1C2C=C(C)CC1)(C)C
Isomeric SMILES CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(C)CC1)(C)C
InChI InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChI Key CYQFCXCEBYINGO-IAGOWNOFSA-N
Classification Click here for help
Compound class Natural product
Approved drug? Yes (FDA (1985))
IUPAC Name Click here for help
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
International Nonproprietary Names Click here for help
INN number INN
5547 dronabinol
Synonyms Click here for help
Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Database Links Click here for help
Specialist databases
GPCRdb Ligand Delta9-tetrahydrocannabinol
Other databases
BindingDB Ligand 50007391
CAS Registry No. 1972-08-3 (source: Scifinder)
ChEBI CHEBI:66964
ChEMBL Ligand CHEMBL465
DrugBank Ligand DB00470
DrugCentral Ligand 4109
GtoPdb PubChem SID 135651250
LIPID MAPS LMPK13120004
PubChem CID 16078
RCSB PDB Ligand TCI
Search Google for chemical match using the InChIKey CYQFCXCEBYINGO-IAGOWNOFSA-N
Search Google for chemicals with the same backbone CYQFCXCEBYINGO
Search PubMed clinical trials dronabinol
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UniChem Compound Search for chemical match using the InChIKey CYQFCXCEBYINGO-IAGOWNOFSA-N
UniChem Connectivity Search for chemical match using the InChIKey CYQFCXCEBYINGO-IAGOWNOFSA-N
Wikipedia Tetrahydrocannabinol