ID: ALA74415

Max Phase: Phase

Molecular Formula: C21H26O2

Molecular Weight: 310.44

Molecule Type: Small molecule

Representations

Synonyms (2): Cannabinol | NSC-134455
Synonyms from Alternative Forms(2):

Canonical SMILES:  CCCCCc1cc(O)c2c(c1)OC(C)(C)c1ccc(C)cc1-2

Standard InChI:  InChI=1S/C21H26O2/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/h9-13,22H,5-8H2,1-4H3

Standard InChI Key:  VBGLYOIFKLUMQG-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 310.44

Molecular Weight (Monoisotopic): 310.1933

AlogP: 5.73

#Rotatable Bonds: 4

Polar Surface Area: 29.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.32

CX Basic pKa:

CX LogP: 6.41

CX LogD: 6.41

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.73

Np Likeness Score: 1.19

References

1. Fichera M, Cruciani G, Bianchi A, Musumarra G..  (2000)  A 3D-QSAR study on the structural requirements for binding to CB(1) and CB(2) cannabinoid receptors.,  43  (12): [PMID:10882356] [10.1021/jm991074s]

2. Bruno-Blanch L, Gálvez J, García-Domenech R..  (2003)  Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.,  13  (16): [PMID:12873507] [10.1016/s0960-894x(03)00535-3]

3. Rhee MH, Vogel Z, Barg J, Bayewitch M, Levy R, Hanus L, Breuer A, Mechoulam R..  (1997)  Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase.,  40  (20): [PMID:9379442] [10.1021/jm970126f]

4. Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK..  (2000)  Novel cannabinol probes for CB1 and CB2 cannabinoid receptors.,  43  (20): [PMID:11020293] [10.1021/jm0001572]

5. Consroe P, Martin AR, Fish BS..  (1982)  Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids.,  25  (5): [PMID:7086846] [10.1021/jm00347a021]

6. Lambert DM, Fowler CJ..  (2005)  The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.,  48  (16): [PMID:16078824] [10.1021/jm058183t]

7. Salo OM, Savinainen JR, Parkkari T, Nevalainen T, Lahtela-Kakkonen M, Gynther J, Laitinen JT, Järvinen T, Poso A..  (2006)  3D-QSAR studies on cannabinoid CB1 receptor agonists: G-protein activation as biological data.,  49  (2): [PMID:16420041] [10.1021/jm0505157]

8. Appendino G, Gibbons S, Giana A, Pagani A, Grassi G, Stavri M, Smith E, Rahman MM..  (2008)  Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.,  71  (8): [PMID:18681481] [10.1021/np8002673]

9. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

10. PubChem BioAssay data set, 

11. Greenberg JH, Mellors A, McGowan JC..  (1978)  Molar volume relationships and the specific inhibition of a synaptosomal enzyme by psychoactive cannabinoids.,  21  (12): [PMID:722729] [10.1021/jm00210a007]

12. Dutour R, Poirier D..  (2017)  Inhibitors of cytochrome P450 (CYP) 1B1.,  135  [PMID:28458135] [10.1016/j.ejmech.2017.04.042]

13. Pollastro F, Caprioglio D, Marotta P, Moriello AS, De Petrocellis L, Taglialatela-Scafati O, Appendino G..  (2018)  Iodine-Promoted Aromatization of p-Menthane-Type Phytocannabinoids.,  81  (3): [PMID:29240420] [10.1021/acs.jnatprod.7b00946]

14. Unpublished dataset, 

15. Nalli Y, Dar MS, Bano N, Rasool JU, Sarkar AR, Banday J, Bhat AQ, Rafia B, Vishwakarma RA, Dar MJ, Ali A..  (2019)  Analyzing the role of cannabinoids as modulators of Wnt/β-catenin signaling pathway for their use in the management of neuropathic pain.,  29  (9): [PMID:30871771] [10.1016/j.bmcl.2019.03.013]

16. Cunningham CW..  (2019)  Plant-Based Modulators of Endocannabinoid Signaling.,  82  (3): [PMID:30816712] [10.1021/acs.jnatprod.8b00874]

17. Caprioglio D, Mattoteia D, Pollastro F, Negri R, Lopatriello A, Chianese G, Minassi A, Collado JA, Munoz E, Taglialatela-Scafati O, Appendino G..  (2020)  The Oxidation of Phytocannabinoids to Cannabinoquinoids.,  83  (5): [PMID:32315173] [10.1021/acs.jnatprod.9b01284]

18. Martin LJ, Cairns EA, Heblinski M, Fletcher C, Krycer JR, Arnold JC, McGregor IS, Bowen MT, Anderson LL..  (2021)  Cannabichromene and Δ⁹-Tetrahydrocannabinolic Acid Identified as Lactate Dehydrogenase-A Inhibitors by in Silico and in Vitro Screening.,  84  (5.0): [PMID:33887133] [10.1021/acs.jnatprod.0c01281]

19. Sampson PB..  (2021)  Phytocannabinoid Pharmacology: Medicinal Properties of Cannabis sativa Constituents Aside from the "Big Two".,  84  (1.0): [PMID:33356248] [10.1021/acs.jnatprod.0c00965]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names