benzyl 4-(((S)-1-((R)-3-(4-(2-cyanophenyl)piperazin-1-yl)-2-hydroxypropoxy)-3-phenylpropan-2-yl)carbamoyl)piperidine-1-carboxylate

ID: ALA5283113

Max Phase: Preclinical

Molecular Formula: C37H45N5O5

Molecular Weight: 639.80

Names and Identifiers

Canonical SMILES:  N#Cc1ccccc1N1CCN(C[C@@H](O)COC[C@H](Cc2ccccc2)NC(=O)C2CCN(C(=O)OCc3ccccc3)CC2)CC1

Standard InChI:  InChI=1S/C37H45N5O5/c38-24-32-13-7-8-14-35(32)41-21-19-40(20-22-41)25-34(43)28-46-27-33(23-29-9-3-1-4-10-29)39-36(44)31-15-17-42(18-16-31)37(45)47-26-30-11-5-2-6-12-30/h1-14,31,33-34,43H,15-23,25-28H2,(H,39,44)/t33-,34+/m0/s1

Standard InChI Key:  FCORXOBTLFNQOU-SZAHLOSFSA-N

Molfile:  

 
     RDKit          2D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -2.4951    2.6629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780    2.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7749    1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    2.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4916    1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4888    0.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713   -0.2177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549    0.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612    1.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7671   -1.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4804   -1.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0494   -1.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0453   -2.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3277   -2.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3277   -3.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848   -3.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991   -3.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923   -2.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750   -2.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3584    3.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3596    2.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6437    2.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9263    2.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292    3.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6455    3.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    3.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982    3.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    3.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    3.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533    3.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3596    3.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0734    3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.6736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7905    3.5045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872    2.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2165    2.6797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    3.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4980    3.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    2.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285    1.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6431    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3596    1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3569    2.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    2.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157    1.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.6230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  3  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
 26 27  1  0
 27  1  1  1
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  1
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 34 39  1  0
 38 39  1  0
 37 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 45 40  1  0
 41 46  1  0
 46 47  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283113

   ---

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: 639.80

Molecular Weight (Monoisotopic): 639.3421

AlogP: 3.83

#Rotatable Bonds: 13

Polar Surface Area: 118.37

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.47

CX LogP: 4.26

CX LogD: 3.92

Aromatic Rings: 3

Heavy Atoms: 47

QED Weighted: 0.29

Np Likeness Score: -1.12

References

1. Huang H, Zhang Y, Xu X, Liu Y, Zhao J, Ma L, Lei J, Ge W, Li N, Ma E, Li Y, Yuan L..  (2023)  Design and synthesis of dual cathepsin L and S inhibitors and antimetastatic activity evaluation in pancreatic cancer cells.,  80  [PMID:36427655] [10.1016/j.bmcl.2022.129087]

Source

Source(1):

• Scientific Literature