Δ9-tetrahydrocannabinol   

GtoPdb Ligand ID: 2424

Abbreviated name: THC
Synonyms: Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Δ9-tetrahydrocannabinol is an approved drug (FDA (1985))
Comment: Δ9-tetrahydrocannabinol is the active ingredient found in cannabis plants (Cannabis sativa). Dronabinol is the INN for the pure, synthetically produced (-)-trans9-tetrahydrocannabinol isomer of tetrahydrocannabinol (shown here).
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2D Structure
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Physico-chemical Properties
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
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
Compound class Natural product or derivative
Approved drug? Yes (FDA (1985))
IUPAC Name
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
International Nonproprietary Names
INN number INN
5547 dronabinol
Synonyms
Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Database Links
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
PubChem CID 16078
RCSB PDB Ligand TCI
Search Google for chemical match using the InChIKey CYQFCXCEBYINGO-IAGOWNOFSA-N
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Search PubMed clinical trials dronabinol
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Search UniChem for chemical match using the InChIKey CYQFCXCEBYINGO-IAGOWNOFSA-N
Search UniChem for chemicals with the same backbone CYQFCXCEBYINGO
Wikipedia Tetrahydrocannabinol