1-((4-Chlorophenylcarbamoyl)methyl)-N-(1-isopropylpiperidin-4-yl)-1H-pyrrole-2-carboxamide

ID: ALA5208176

PubChem CID: 168296113

Max Phase: Preclinical

Molecular Formula: C21H27ClN4O2

Molecular Weight: 402.93

Names and Identifiers

Canonical SMILES:  CC(C)N1CCC(NC(=O)c2cccn2CC(=O)Nc2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C21H27ClN4O2/c1-15(2)25-12-9-18(10-13-25)24-21(28)19-4-3-11-26(19)14-20(27)23-17-7-5-16(22)6-8-17/h3-8,11,15,18H,9-10,12-14H2,1-2H3,(H,23,27)(H,24,28)

Standard InChI Key:  ZCTIETKJPBPXKY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.8253    1.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    2.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    2.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503    2.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    2.0326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503    1.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    2.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999    2.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119    2.0326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8242    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119    0.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1335    0.6515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176    0.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176    1.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1335    1.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033   -0.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -1.5249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2999   -0.5148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4931   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   -1.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1157   -1.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977   -2.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4813   -2.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788   -2.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8944   -2.3792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 14 12  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 12  2  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208176

   ---

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: 402.93

Molecular Weight (Monoisotopic): 402.1823

AlogP: 3.38

#Rotatable Bonds: 6

Polar Surface Area: 66.37

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.29

CX Basic pKa: 9.16

CX LogP: 2.59

CX LogD: 0.83

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.78

Np Likeness Score: -2.09

References

1. Fernández-Bachiller MI, Hwang S, Schembri ME, Lindemann P, Guberman M, Herziger S, Specker E, Matter H, Will DW, Czech J, Wagner M, Bauer A, Schreuder H, Ritter K, Urmann M, Wehner V, Sun H, Nazaré M..  (2022)  Probing Factor Xa Protein-Ligand Interactions: Accurate Free Energy Calculations and Experimental Validations of Two Series of High-Affinity Ligands.,  65  (19.0): [PMID:36178213] [10.1021/acs.jmedchem.2c00865]

Source

Source(1):

• Scientific Literature