3-((4-((2-methoxybenzo[d]thiazol-6-yl)amino)-5methylpyrimidin-2-yl)amino)benzenesulfonamide

ID: ALA5203476

PubChem CID: 168293034

Max Phase: Preclinical

Molecular Formula: C19H18N6O3S2

Molecular Weight: 442.53

Names and Identifiers

Canonical SMILES:  COc1nc2ccc(Nc3nc(Nc4cccc(S(N)(=O)=O)c4)ncc3C)cc2s1

Standard InChI:  InChI=1S/C19H18N6O3S2/c1-11-10-21-18(23-12-4-3-5-14(8-12)30(20,26)27)25-17(11)22-13-6-7-15-16(9-13)29-19(24-15)28-2/h3-10H,1-2H3,(H2,20,26,27)(H2,21,22,23,25)

Standard InChI Key:  NHMYKQBJKFHAAT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -4.3047    0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8338   -0.3074    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0296   -0.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0296    0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126    1.0139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3194    1.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030    0.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030   -0.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8885   -0.4693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5433   -0.4710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551   -0.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9696   -0.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -0.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4016   -0.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1132   -0.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278   -0.4650    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4145   -1.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2394   -1.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422   -0.0526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1132    0.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970    1.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840    0.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551    0.7662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387    1.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1738    0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883    1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5422   -0.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  2  0
  5  6  1  0
  6  2  2  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  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 18 23  1  0
 23 24  2  0
 24 25  1  0
 25 16  2  0
 14 26  1  0
 26 27  2  0
 27 28  1  0
 28 12  2  0
 28 29  1  0
  1 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203476

   ---

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: 442.53

Molecular Weight (Monoisotopic): 442.0882

AlogP: 3.54

#Rotatable Bonds: 6

Polar Surface Area: 132.12

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.24

CX Basic pKa: 4.25

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: -1.95

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