tert-butyl 4-((6-((4-(benzo[d]thiazol-5-yl)-5-methoxypyrimidin-2-yl)amino)pyridin-3-yl)methyl)piperazine-1-carboxylate

ID: ALA5288208

Max Phase: Preclinical

Molecular Formula: C27H31N7O3S

Molecular Weight: 533.66

Names and Identifiers

Canonical SMILES:  COc1cnc(Nc2ccc(CN3CCN(C(=O)OC(C)(C)C)CC3)cn2)nc1-c1ccc2scnc2c1

Standard InChI:  InChI=1S/C27H31N7O3S/c1-27(2,3)37-26(35)34-11-9-33(10-12-34)16-18-5-8-23(28-14-18)31-25-29-15-21(36-4)24(32-25)19-6-7-22-20(13-19)30-17-38-22/h5-8,13-15,17H,9-12,16H2,1-4H3,(H,28,29,31,32)

Standard InChI Key:  VZSXVSXSMKEFRN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -3.2103    1.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    0.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5024   -0.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5024   -0.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923   -1.4132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923   -2.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0866   -2.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3668   -2.2525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448   -2.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7735   -2.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4932   -2.2693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4932   -1.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2097   -1.0365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2097   -0.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9251    0.1999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9251    1.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123    1.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123    2.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9289    2.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968    1.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823    1.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823    2.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0679    2.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    2.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4309    2.5200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9159    1.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4309    1.1850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    1.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0679    1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968    0.2022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7819   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622   -1.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3668   -1.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -1.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2210   -1.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9205    0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9289   -0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 25  1  0
 29 30  2  0
 30 22  1  0
 21 31  2  0
 31 15  1  0
 13 32  1  0
 32 33  2  0
 33 10  1  0
  8 34  1  0
 34 35  1  0
 35  5  1  0
  4 36  2  0
  2 37  1  0
  2 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5288208

   ---

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: 533.66

Molecular Weight (Monoisotopic): 533.2209

AlogP: 4.95

#Rotatable Bonds: 6

Polar Surface Area: 105.60

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.14

CX Basic pKa: 5.93

CX LogP: 4.25

CX LogD: 4.24

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.37

Np Likeness Score: -1.53

References

1. Yuan K, Shen H, Zheng M, Xia F, Li Q, Chen W, Ji M, Yang H, Zhuang X, Cai Z, Min W, Wang X, Xiao Y, Yang P..  (2023)  Discovery of Potent DYRK2 Inhibitors with High Selectivity, Great Solubility, and Excellent Safety Properties for the Treatment of Prostate Cancer.,  66  (6): [PMID:36800260] [10.1021/acs.jmedchem.3c00106]

Source

Source(1):

• Scientific Literature