3-((5-methyl-4-((2-oxo-2,3-dihydro-1Hbenzo[d]imidazol-5-yl)amino)pyrimidin-2yl)amino)benzenesulfonamide

ID: ALA5199794

PubChem CID: 66659290

Max Phase: Preclinical

Molecular Formula: C18H17N7O3S

Molecular Weight: 411.45

Names and Identifiers

Canonical SMILES:  Cc1cnc(Nc2cccc(S(N)(=O)=O)c2)nc1Nc1ccc2[nH]c(=O)[nH]c2c1

Standard InChI:  InChI=1S/C18H17N7O3S/c1-10-9-20-17(22-11-3-2-4-13(7-11)29(19,27)28)25-16(10)21-12-5-6-14-15(8-12)24-18(26)23-14/h2-9H,1H3,(H2,19,27,28)(H2,23,24,26)(H2,20,21,22,25)

Standard InChI Key:  HYXCUHJMQLHGDS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -4.5109    0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0401   -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    0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0189    1.0139    0.0000 N   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    0.7717    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   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3372   -0.4710    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
    1.7633   -0.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -0.0547    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
    3.9070   -0.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6215   -0.4650    0.0000 S   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
    5.0332   -1.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -0.0526    0.0000 N   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
    3.1907    1.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777    0.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    0.7662    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    0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0945    1.1807    0.0000 C   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
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA5199794

   3-[[5-Methyl-4-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide

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: 411.45

Molecular Weight (Monoisotopic): 411.1114

AlogP: 2.09

#Rotatable Bonds: 5

Polar Surface Area: 158.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.24

CX Basic pKa: 4.25

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -1.75

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