N-((1RS,2SR)-2-aminocyclohexyl)-5-methyl-4-(6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl)thiophene-2-carboxamide

ID: ALA4550486

PubChem CID: 59603906

Max Phase: Preclinical

Molecular Formula: C22H25N7OS

Molecular Weight: 435.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1sc(C(=O)N[C@@H]2CCCC[C@@H]2N)cc1-c1cnn2cc(-c3cnn(C)c3)cnc12

Standard InChI:  InChI=1S/C22H25N7OS/c1-13-16(7-20(31-13)22(30)27-19-6-4-3-5-18(19)23)17-10-26-29-12-14(8-24-21(17)29)15-9-25-28(2)11-15/h7-12,18-19H,3-6,23H2,1-2H3,(H,27,30)/t18-,19+/m0/s1

Standard InChI Key:  HZYWBSPIPUYOAD-RBUKOAKNSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   17.3055  -11.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3055  -12.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0108  -12.4188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0108  -10.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7160  -11.1972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7160  -12.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4941  -12.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9752  -11.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4942  -10.9444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7483  -13.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2679  -13.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7482  -14.3719    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5255  -14.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5254  -13.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1866  -14.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1012  -15.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9331  -14.2674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5940  -10.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5061   -9.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7063   -9.8075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2998  -10.5164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8484  -11.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3717   -9.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5943  -14.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4507  -13.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5049  -15.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1620  -16.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9106  -15.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9981  -14.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3370  -14.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4222  -13.5999    0.0000 N   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 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
  1 18  1  0
 20 23  1  0
 24 17  1  1
 11 25  1  0
 24 26  1  0
 24 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4550486

   N-[(1R,2S)-2-aminocyclohexyl]-5-methyl-4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]thiophene-2-carboxamide

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: 435.56

Molecular Weight (Monoisotopic): 435.1841

AlogP: 3.17

#Rotatable Bonds: 4

Polar Surface Area: 103.13

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.46

CX LogP: 2.63

CX LogD: 0.60

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: -1.60

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