3-chloro-4-(6-((1S,5S)-8-(cyclopropylsulfonyl)-8-azabicyclo[3.2.1]octan-3-yloxy)-5-methylpyrimidin-4-ylamino)benzonitrile

ID: ALA3084389

PubChem CID: 53235503

Max Phase: Preclinical

Molecular Formula: C22H24ClN5O3S

Molecular Weight: 473.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Nc2ccc(C#N)cc2Cl)ncnc1O[C@H]1C[C@H]2CC[C@@H](C1)N2S(=O)(=O)C1CC1

Standard InChI:  InChI=1S/C22H24ClN5O3S/c1-13-21(27-20-7-2-14(11-24)8-19(20)23)25-12-26-22(13)31-17-9-15-3-4-16(10-17)28(15)32(29,30)18-5-6-18/h2,7-8,12,15-18H,3-6,9-10H2,1H3,(H,25,26,27)/t15-,16+,17+

Standard InChI Key:  JONDVPWMQDOELC-FVQHAEBGSA-N

Molfile:  

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    9.8137  -30.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3084389

   3-chloro-4-[[6-[[(1S,5R)-8-cyclopropylsulfonyl-8-azabicyclo[3.2.1]octan-3-yl]oxy]-5-methylpyrimidin-4-yl]amino]benzonitrile

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: 473.99

Molecular Weight (Monoisotopic): 473.1288

AlogP: 3.92

#Rotatable Bonds: 6

Polar Surface Area: 108.21

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.04

CX Basic pKa: 3.69

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.68

Np Likeness Score: -1.26

References

1. Xia Y, Chackalamannil S, Greenlee WJ, Jayne C, Neustadt B, Stamford A, Vaccaro H, Xu XL, Baker H, O'Neill K, Woods M, Hawes B, Kowalski T..  (2011)  Discovery of a nortropanol derivative as a potent and orally active GPR119 agonist for type 2 diabetes.,  21  (11): [PMID:21536438] [10.1016/j.bmcl.2011.04.035]

Source

Source(1):

• Scientific Literature