ID: ALA2312346

Max Phase: Preclinical

Molecular Formula: C23H27NO4

Molecular Weight: 381.47

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(CCOC(=O)C2=C(c3ccccc3)CCN(C)C2)cc1OC

Standard InChI:  InChI=1S/C23H27NO4/c1-24-13-11-19(18-7-5-4-6-8-18)20(16-24)23(25)28-14-12-17-9-10-21(26-2)22(15-17)27-3/h4-10,15H,11-14,16H2,1-3H3

Standard InChI Key:  GYBGSRCFWGEOKR-UHFFFAOYSA-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: 381.47

Molecular Weight (Monoisotopic): 381.1940

AlogP: 3.58

#Rotatable Bonds: 7

Polar Surface Area: 48.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.92

CX LogP: 3.86

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: 0.02

References

1. Zheng G, Smith AM, Huang X, Subramanian KL, Siripurapu KB, Deaciuc A, Zhan CG, Dwoskin LP..  (2013)  Structural modifications to tetrahydropyridine-3-carboxylate esters en route to the discovery of M5-preferring muscarinic receptor orthosteric antagonists.,  56  (4): [PMID:23379472] [10.1021/jm301774u]

2. Garrison AT, Orsi DL, Capstick RA, Whomble D, Li J, Carter TR, Felts AS, Vinson PN, Rodriguez AL, Han A, Hajari K, Cho HP, Teal LB, Ragland MG, Ghamari-Langroudi M, Bubser M, Chang S, Schnetz-Boutaud NC, Boutaud O, Blobaum AL, Foster DJ, Niswender CM, Conn PJ, Lindsley CW, Jones CK, Han C..  (2022)  Development of VU6019650: A Potent, Highly Selective, and Systemically Active Orthosteric Antagonist of the M₅ Muscarinic Acetylcholine Receptor for the Treatment of Opioid Use Disorder.,  65  (8.0): [PMID:35417155] [10.1021/acs.jmedchem.2c00192]

Source

Source(1):

• Scientific Literature