(3S,8aR)-N-((S)-1-cyano-2-(4'-cyanobiphenyl-4-yl)ethyl)octahydropyrrolo[1,2-a]pyrazine-3-carboxamide

ID: ALA4879373

PubChem CID: 164628401

Max Phase: Preclinical

Molecular Formula: C24H25N5O

Molecular Weight: 399.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(-c2ccc(C[C@@H](C#N)NC(=O)[C@@H]3CN4CCC[C@@H]4CN3)cc2)cc1

Standard InChI:  InChI=1S/C24H25N5O/c25-13-18-5-9-20(10-6-18)19-7-3-17(4-8-19)12-21(14-26)28-24(30)23-16-29-11-1-2-22(29)15-27-23/h3-10,21-23,27H,1-2,11-12,15-16H2,(H,28,30)/t21-,22+,23-/m0/s1

Standard InChI Key:  BQWJEMPWVHELPK-ZRBLBEILSA-N

Molfile:  

 
     RDKit          2D

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    5.7346  -26.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7334  -27.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4481  -28.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1643  -27.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1615  -26.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4463  -26.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8793  -28.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8757  -28.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5897  -29.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3044  -28.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3005  -27.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5858  -27.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0199  -29.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7354  -29.6495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0202  -26.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0200  -25.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7342  -25.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3057  -25.1189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4484  -24.7060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5915  -25.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917  -26.3562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8771  -25.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8773  -24.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486  -25.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1634  -25.5335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505  -24.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698  -23.8797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0008  -23.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1769  -22.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369  -23.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332  -24.6978    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 10 13  1  0
 13 14  3  0
  1 15  1  0
 16 15  1  6
 16 17  1  0
 16 18  1  0
 17 19  3  0
 18 20  1  0
 20 21  2  0
 22 20  1  1
 22 23  1  0
 22 25  1  0
 23 27  1  0
 26 24  1  0
 24 25  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
 26 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4879373

   ---

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: 399.50

Molecular Weight (Monoisotopic): 399.2059

AlogP: 2.21

#Rotatable Bonds: 5

Polar Surface Area: 91.95

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.02

CX Basic pKa: 9.35

CX LogP: 2.49

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.80

Np Likeness Score: -0.65

References

1. Banerjee A, Velagaleti R, Patil S, Pawar M, Yadav P, Kadam P, Qadri MM, Chakraborti S, Saini JS, Behera DB, Karanjai K, Iyer PS, Gharat LA, Das S..  (2021)  Development of potent and selective Cathepsin C inhibitors free of aortic binding liability by application of a conformational restriction strategy.,  47  [PMID:34139325] [10.1016/j.bmcl.2021.128202]

Source

Source(1):

• Scientific Literature