5-((5-methyl-2-((3(methylsulfonyl)phenyl)amino)pyrimidin-4yl)amino)benzo[d]oxazol-2(3H)-one

ID: ALA5191312

Cas Number: 1236670-88-4

PubChem CID: 77105030

Max Phase: Preclinical

Molecular Formula: C19H17N5O4S

Molecular Weight: 411.44

Names and Identifiers

Canonical SMILES:  Cc1cnc(Nc2cccc(S(C)(=O)=O)c2)nc1Nc1ccc2oc(=O)[nH]c2c1

Standard InChI:  InChI=1S/C19H17N5O4S/c1-11-10-20-18(22-12-4-3-5-14(8-12)29(2,26)27)24-17(11)21-13-6-7-16-15(9-13)23-19(25)28-16/h3-10H,1-2H3,(H,23,25)(H2,20,21,22,24)

Standard InChI Key:  MEPRAIGNNALDJA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -5.3360    0.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5110    0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0402   -0.3074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -0.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0188    1.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257    1.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8093    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8093   -0.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239   -0.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -0.4693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3801   -0.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -0.4711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    0.7661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3325    1.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3801    0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4778   -0.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4778    0.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    1.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9070    0.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9070   -0.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1953   -0.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6215   -0.4651    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3360   -0.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -1.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340   -1.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  0
  5  4  2  0
  5  6  1  0
  6  2  1  0
  7  5  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 12  2  0
 17 18  1  0
 14 19  1  0
 19 20  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 20 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 26 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5191312

   5-[[5-Methyl-2-[[3-(methylsulfonyl)phenyl]amino]-4-pyrimidinyl]amino]-2(3H)-benzoxazolone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 411.44

Molecular Weight (Monoisotopic): 411.1001

AlogP: 3.11

#Rotatable Bonds: 5

Polar Surface Area: 129.98

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.45

CX Basic pKa: 4.27

CX LogP: 2.91

CX LogD: 2.91

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -1.54

References

1. Chen Y, Li H, Yen R, Heckrodt TJ, McMurtrie D, Singh R, Taylor V, Masuda ES, Park G, Payan DG..  (2022)  Optimization of Pyrimidine Compounds as Potent JAK1 Inhibitors and the Discovery of R507 as a Clinical Candidate.,  13  (11.0): [PMID:36385926] [10.1021/acsmedchemlett.2c00411]

Source

Source(1):

• Scientific Literature