(1'S,3'R,4'S)-N-(6-phenylpyrimidin-4-yl)-4H-1'-azaspiro[oxazole-5,3'-bicyclo[2.2.2]octan]-2-amine

ID: ALA4102566

Chembl Id: CHEMBL4102566

PubChem CID: 52920236

Max Phase: Preclinical

Molecular Formula: C19H21N5O

Molecular Weight: 335.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(-c2cc(NC3=NC[C@@]4(CN5CCC4CC5)O3)ncn2)cc1

Standard InChI:  InChI=1S/C19H21N5O/c1-2-4-14(5-3-1)16-10-17(22-13-21-16)23-18-20-11-19(25-18)12-24-8-6-15(19)7-9-24/h1-5,10,13,15H,6-9,11-12H2,(H,20,21,22,23)/t19-/m0/s1

Standard InChI Key:  WVNOFRZQUMORMI-IBGZPJMESA-N

Alternative Forms

1. Parent:

   

   ALA4102566

   (3R)-N-(6-phenylpyrimidin-4-yl)spiro[1-azabicyclo[2.2.2]octane-3,5'-4H-1,3-oxazole]-2'-amine

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

Calculated Properties

Molecular Weight: 335.41

Molecular Weight (Monoisotopic): 335.1746

AlogP: 2.41

#Rotatable Bonds: 2

Polar Surface Area: 62.64

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.50

CX LogP: 2.87

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.91

Np Likeness Score: -0.11

References

1. Iwuagwu C, King D, McDonald IM, Cook J, Zusi FC, Hill MD, Mate RA, Fang H, Knox R, Gallagher L, Post-Munson Amy Easton D, Miller R, Benitex Y, Siuciak J, Lodge N, Zaczek R, Morgan D, Bristow L, Macor JE, Olson RE..  (2017)  Design and synthesis of a novel series of 4-heteroarylamino-1'-azaspiro[oxazole-5,3'-bicyclo[2.2.2]octanes as α7 nicotinic receptor agonists 2. Development of 4-heteroaryl SAR.,  27  (5): [PMID:28169167] [10.1016/j.bmcl.2017.01.058]

2. King D, Iwuagwu C, Cook J, McDonald IM, Mate R, Zusi FC, Hill MD, Fang H, Zhao R, Wang B, Easton AE, Miller R, Post-Munson D, Knox RJ, Gallagher L, Westphal R, Molski T, Fan J, Clarke W, Benitex Y, Lentz KA, Denton R, Morgan D, Zaczek R, Lodge NJ, Bristow LJ, Macor JE, Olson RE..  (2017)  BMS-933043, a Selective α7 nAChR Partial Agonist for the Treatment of Cognitive Deficits Associated with Schizophrenia.,  8  (3): [PMID:28337332] [10.1021/acsmedchemlett.7b00032]

Source

Source(1):

• Scientific Literature