N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide

ID: ALA4552628

Cas Number: 1314893-26-9

PubChem CID: 89735655

Max Phase: Preclinical

Molecular Formula: C18H18ClF2N5OS

Molecular Weight: 425.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1sc(C(=O)N[C@@H]2[C@H](N)CCCC2(F)F)cc1-c1cnn2cc(Cl)cnc12

Standard InChI:  InChI=1S/C18H18ClF2N5OS/c1-9-11(12-7-24-26-8-10(19)6-23-16(12)26)5-14(28-9)17(27)25-15-13(22)3-2-4-18(15,20)21/h5-8,13,15H,2-4,22H2,1H3,(H,25,27)/t13-,15-/m1/s1

Standard InChI Key:  NGFGTMFVWSDFPS-UKRRQHHQSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   31.4495  -18.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4495  -19.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1548  -19.8685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1548  -18.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8600  -18.6468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8600  -19.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6382  -19.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1192  -19.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6382  -18.3941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8923  -20.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4119  -21.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8922  -21.8215    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.6695  -21.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6694  -20.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3306  -22.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2452  -22.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0771  -21.7170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7383  -22.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5947  -21.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6490  -23.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3060  -23.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0546  -23.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1421  -22.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4810  -21.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5662  -21.0496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7406  -18.2403    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.8532  -22.7947    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.2329  -23.7151    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  2  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
  7 10  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 18 17  1  6
 11 19  1  0
 18 20  1  0
 18 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
  1 26  1  0
 20 27  1  0
 20 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552628

   Mark-IN-2

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 425.89

Molecular Weight (Monoisotopic): 425.0889

AlogP: 3.66

#Rotatable Bonds: 3

Polar Surface Area: 85.31

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.28

CX LogP: 3.18

CX LogD: 1.32

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -1.18

References

1. Sloman DL, Noucti N, Altman MD, Chen D, Mislak AC, Szewczak A, Hayashi M, Warren L, Dellovade T, Wu Z, Marcus J, Walker D, Su HP, Edavettal SC, Munshi S, Hutton M, Nuthall H, Stanton MG..  (2016)  Optimization of microtubule affinity regulating kinase (MARK) inhibitors with improved physical properties.,  26  (17): [PMID:27491711] [10.1016/j.bmcl.2016.02.003]

Source

Source(1):

• Scientific Literature