Table 1.
Phytocannabinoids presenting AI profiles. The information obtained from molecular docking of the 45 cannabinoids considered as promising AIs, such as the bind affinity score and the description of the most important interactions, is presented. The information regarding CBG and CBN is also presented.
| Cannabinoid Name | Cannabinoid Class | Binding Affinity (kcal/mol) | Relevant Interactions |
|---|---|---|---|
| 8-Oxo-(-)-Δ9-trans-tetrahydrocannabinol | Δ9-THC | −9.2 | Hydrogen bonds with Arg115 and Leu477; hydrophobic interactions with Trp224 and Phe221 |
| 11-Acetoxy-(-)-Δ9-trans-tetrahydrocannabinolic acid A | Δ9-THC | −8.3 | Hydrogen bonds with Arg115, Met374, Asp309, and Leu477; hydrophobic interactions with Phe221 |
| (-)-Δ9-trans-Tetrahydrocannabivarinic acid | Δ9-THC | −7.1 | Hydrogen bonds with the heme group, Leu372, and Leu477; hydrophobic interactions with Trp224 and Phe221 |
| (-)-Δ9-trans-Tetrahydrocannabinolic acid A-C4 | Δ9-THC | −6.7 | Hydrogen bonds with the heme group, Leu372, Met374, and Leu477; hydrophobic interactions with Trp224 and Phe221 |
| (-)-Δ9-trans-Tetrahydrocannabinolic acid B | Δ9-THC | −6.0 | Hydrogen bonds with Asp309 and Leu477; hydrophobic interactions with Trp224 and Phe221 |
| Δ8-trans-Tetrahydrocannabinolic acid A | Δ9-THC | −4.4 | Hydrogen bond with Asp309; hydrophobic interactions with Phe221 |
| (-)-Δ9-trans-Tetrahydrocannabinal | Δ9-THC | −3.8 | Hydrogen bond with Asp309; hydrophobic interactions with Trp224 and Phe221 |
| Cannabidiol (CBD) | Cannabidiol | −8.7 | Hydrogen bond with Asp309; hydrophobic interactions with Phe221 |
| Cannabidiorcol | Cannabidiol | −7.8 | Hydrogen bonds with Asp309 and Leu477; hydrophobic interactions with Phe221 |
| (-)-Cannabidivarin (CBDV) | Cannabidiol | −7.6 | Hydrogen bonds with Asp309 and Leu477; hydrophobic interactions with Phe221 |
| Cannabidiol monomethylether (CBDM) | Cannabidiol | −7.3 | Hydrogen bonds with Asp309 and Ser478; hydrophobic interactions with Phe221 |
| Cannabidiol-C4 (CBDB) | Cannabidiol | −6.9 | Hydrogen bonds with Asp309 and Leu477; hydrophobic interactions with Phe221 |
| Cannabidivarinic acid | Cannabidiol | −6.6 | Hydrogen bonds with Asp309 and Leu477; hydrophobic interactions with Phe221 |
| Cannabidiolic acid (CBDA) | Cannabidiol | −5.7 | Hydrogen bonds with Asp309 and Leu477; hydrophobic interactions with Phe221 |
| Cannabigerol (CBG) | Cannabigerol | −6.1 | Hydrophobic interactions with Phe221 and Trp224 |
| Cannabinerolic acid | Cannabigerol | −6.7 | Hydrogen bond with Asp309; hydrophobic interactions with Trp224 and Phe221 |
| Camagerol | Cannabigerol | −6.6 | Hydrogen bonds with Asp309, Arg115, and Met374 |
| (-)-6,7-cis-Epoxycannabigerolic acid | Cannabigerol | −6.3 | Hydrogen bonds with Asp309, Leu477, and Arg115; hydrophobic interactions with Trp224 |
| Cannabigerovarinic acid (CBGVA) | Cannabigerol | −5.8 | Hydrogen bond with Asp309 |
| 5-Acetyl-4-hydroxy cannabigerol | Cannabigerol | −5.1 | Hydrogen bond with Asp309; hydrophobic interactions with Phe221 |
| (-)-6,7-trans-Epoxycannabigerolic acid | Cannabigerol | −5.4 | Hydrogen bonds with Asp309 and Leu477; hydrophobic interactions with Trp224 |
| Cannabielsoic acid B-C3 | Cannabielsoin | −6.0 | Hydrogen bonds with the heme group and Asp309 |
| Cannabielsoin acid A | Cannabielsoin | −5.9 | Hydrogen bonds with Asp309 and Arg115 |
| Cannabielsoin acid B | Cannabielsoin | −5.1 | Hydrogen bond with Asp309; hydrophobic interactions with Trp224 and Phe221 |
| Cannabicyclol | Cannabicyclol | −9.8 | Hydrogen bond with Asp309; hydrophobic interactions with Phe221 |
| Cannabicyclovarin | Cannabicyclol | −9.3 | Hydrogen bond with Asp309; hydrophobic interactions with Phe221 |
| Cannabicyclolic acid | Cannabicyclol | −5.5 | Hydrogen bond with Leu477 |
| Cannabichromevarin | Cannabichromene | −7.1 | Hydrogen bond with Asp309 |
| Cannabichromenic acid (CBCA) | Cannabichromene | −6.4 | Hydrogen bond with Asp309; hydrophobic interactions with Trp224 |
| Cannabichromene (CBC) | Cannabichromene | −6.0 | Hydrogen bond with Asp309; hydrophobic interactions with Phe221 |
| (-)-7-Hydroxycannabichromene | Cannabichromene | −5.5 | Hydrogen bonds with the heme group and Asp309; hydrophobic interactions with Phe221 |
| Cannabichromevarinic acid | Cannabichromene | −5.2 | Hydrogen bond with Arg115 |
| Cannabinol (CBN) | Cannabinol | −5.9 | Hydrogen bond with Leu477; hydrophobic interactions with Phe221 and Trp224 |
| 8-Hydroxycannabinol | Cannabinol | −7.9 | Hydrogen bonds with Asp309 and Arg115 |
| Cannabiorcol-C1 | Cannabinol | −6.6 | Hydrogen bond with Asp309; hydrophobic interactions with Trp224 and Phe221 |
| 8-Hydroxycannabinolic acid A | Cannabinol | −4.8 | Hydrogen bonds with Asp309 and Arg115; hydrophobic interactions with Trp224 and Phe221 |
| (-)-trans-Cannabitriol-OEt-C5 * | Cannabitriol | −3.9 | Hydrogen bonds with Asp309, Arg115, and Leu477; hydrophobic interactions with Phe221 |
| (-)-trans-Cannabitriol-OEt-C3 * | Cannabitriol | −3.5 | Hydrogen bonds with Asp309 and Ser478; hydrophobic interactions with Phe221 |
| (-)-Δ7-trans-(1R,3R,6R)-isotetrahydrocannabinol-C5 | Miscellaneous | −9.8 | Hydrogen bonds with the heme group and Asp309; hydrophobic interactions with Trp224 and Phe221 |
| Cannabimovone | Miscellaneous | −8.4 | Hydrogen bond with Asp309; hydrophobic interactions with Phe221 |
| Cannabichromanone C | Miscellaneous | −7.8 | Hydrogen bonds with Asp309 and Arg115; hydrophobic interactions with Phe221 |
| Dehydrocannabifuran | Miscellaneous | −7.3 | Hydrogen bond with Asp309; hydrophobic interactions with Phe221 |
| Cannabichromanone B | Miscellaneous | −7.0 | Hydrogen bonds with the heme group and Asp309; hydrophobic interactions with Phe221 |
| (-)-(7R)-Cannabicoumarononic acid | Miscellaneous | −6.5 | Hydrogen bonds with Asp309 and Met374; hydrophobic interactions with Trp224 and Phe221 |
| 8-Hydroxy-isohexahydrocannabivarin | Miscellaneous | −6.0 | Hydrogen bonds with the heme group and Asp309; hydrophobic interactions with Trp224 and Phe221 |
| Cannabicoumaronome-C5 | Miscellaneous | −6.0 | Hydrogen bonds with the heme group and Asp309; hydrophobic interactions with Phe221 |
| Cannabichromanone-C3 | Miscellaneous | −5.4 | Hydrogen bonds with the heme group and Asp309; hydrophobic interactions with Phe221 |
* Et = ethyl.