ID: ALA463843

Max Phase: Preclinical

Molecular Formula: C22H32O4

Molecular Weight: 360.49

Molecule Type: Small molecule

Representations

Synonyms (1): Cannabigerolic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCCCc1cc(O)c(C/C=C(\C)CCC=C(C)C)c(O)c1C(=O)O

Standard InChI:  InChI=1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26)/b16-12+

Standard InChI Key:  SEEZIOZEUUMJME-FOWTUZBSSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 360.49

Molecular Weight (Monoisotopic): 360.2301

AlogP: 5.76

#Rotatable Bonds: 10

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.92

CX Basic pKa:

CX LogP: 7.35

CX LogD: 3.87

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.37

Np Likeness Score: 2.15

References

1. Ahmed SA, Ross SA, Slade D, Radwan MM, Zulfiqar F, Matsumoto RR, Xu YT, Viard E, Speth RC, Karamyan VT, ElSohly MA..  (2008)  Cannabinoid ester constituents from high-potency Cannabis sativa.,  71  (4): [PMID:18303850] [10.1021/np070454a]

2. 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]

3. Anderson LL, Low IK, Banister SD, McGregor IS, Arnold JC..  (2019)  Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.,  82  (11): [PMID:31686510] [10.1021/acs.jnatprod.9b00600]

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

5. 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]

6. van Breemen RB, Muchiri RN, Bates TA, Weinstein JB, Leier HC, Farley S, Tafesse FG..  (2022)  Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.,  85  (1.0): [PMID:35007072] [10.1021/acs.jnatprod.1c00946]

Source

Source(1):

• Scientific Literature