tert-Butyl (amino(4-((8-(1-(pyrrolidine-1-carbonyl)cyclopentyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-1-yl)methyl)phenyl)methylene)carbamate

ID: ALA3960020

Max Phase: Preclinical

Molecular Formula: C33H42N6O3

Molecular Weight: 570.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)/N=C(\N)c1ccc(CC2NCCn3c2nc2cc(C4(C(=O)N5CCCC5)CCCC4)ccc23)cc1

Standard InChI:  InChI=1S/C33H42N6O3/c1-32(2,3)42-31(41)37-28(34)23-10-8-22(9-11-23)20-26-29-36-25-21-24(12-13-27(25)39(29)19-16-35-26)33(14-4-5-15-33)30(40)38-17-6-7-18-38/h8-13,21,26,35H,4-7,14-20H2,1-3H3,(H2,34,37,41)

Standard InChI Key:  IQOBXOFWCZUJLD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 42 47  0  0  0  0  0  0  0  0999 V2000
   16.5750   -6.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5791   -7.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2884   -7.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3832   -8.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5594   -8.4135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8325   -9.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7578   -7.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1848   -9.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3598   -9.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9472   -9.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1223   -9.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7098   -9.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1223   -8.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9472   -8.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8848   -9.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6473   -8.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4723   -8.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2348   -7.7197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8848   -7.7197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4723   -7.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6473   -7.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0952   -9.0473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3416   -8.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4278   -7.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7604   -7.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0067   -7.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9205   -8.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5879   -9.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1668   -8.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3598   -9.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2736   -9.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0272  -10.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5793   -9.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9119   -8.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4311   -7.4721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970   -7.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5137   -8.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786   -8.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077   -7.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7225   -7.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5973   -9.8632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0289   -8.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  6  2  0
  4  7  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
 16 17  1  0
 16 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 18 21  1  0
 22 23  1  0
 23 24  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 23 28  2  0
 24 25  2  0
 18 24  1  0
 16 22  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 29 33  1  0
 34 35  2  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 36 40  1  0
 34 36  1  0
 29 34  1  0
 27 29  1  0
 15 17  1  0
 12 15  1  0
  8  9  1  0
  8 41  1  0
  5  8  2  0
  7  2  1  0
  2 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3960020

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 570.74

Molecular Weight (Monoisotopic): 570.3318

AlogP: 5.00

#Rotatable Bonds: 5

Polar Surface Area: 114.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.55

CX LogP: 4.51

CX LogD: 4.13

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.33

Np Likeness Score: -0.64

References

1. Chen D, Shi J, Liu J, Zhang X, Deng X, Yang Y, Cui S, Zhu Q, Gong G, Xu Y..  (2017)  Design, synthesis and antithrombotic evaluation of novel non-peptide thrombin inhibitors.,  25  (2): [PMID:27884512] [10.1016/j.bmc.2016.11.012]

Source

Source(1):

• Scientific Literature