(S)-N-(4-Chlorobenzyl)-1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)pyrrolidine-2-carboxamide

ID: ALA2063867

PubChem CID: 57522926

Max Phase: Preclinical

Molecular Formula: C24H35ClN4O3

Molecular Weight: 463.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H](C)C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)NCc1ccc(Cl)cc1)C1CCCCC1

Standard InChI:  InChI=1S/C24H35ClN4O3/c1-16(26-2)22(30)28-21(18-7-4-3-5-8-18)24(32)29-14-6-9-20(29)23(31)27-15-17-10-12-19(25)13-11-17/h10-13,16,18,20-21,26H,3-9,14-15H2,1-2H3,(H,27,31)(H,28,30)/t16-,20-,21-/m0/s1

Standard InChI Key:  MNWPVYOXWIATDM-NDXORKPFSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   11.5875  -11.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3020  -11.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8110  -11.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3064  -12.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7715  -12.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5632  -12.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3020  -10.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0164  -11.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0164  -12.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7309  -11.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4454  -11.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4454  -12.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1599  -11.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8743  -11.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1599  -10.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4010  -10.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8160  -10.0342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5760  -10.7443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1610  -11.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5888  -11.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3020  -12.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3000  -13.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0126  -14.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7289  -13.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7326  -12.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3360  -11.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9304  -10.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1061  -10.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6903  -11.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1047  -12.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9276  -12.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8653  -11.4435    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3 16  1  1
  2  8  1  0
 16 17  2  0
 16 18  1  0
  8  9  1  1
 18 19  1  0
  3  4  1  0
 14 20  1  0
  9 21  1  0
  8 10  1  0
  4  5  1  0
 10 11  1  0
  5  6  1  0
 11 12  2  0
  9 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  6  1  1  0
 19 26  1  0
 11 13  1  0
 26 27  2  0
  1  2  1  0
 27 28  1  0
 13 14  1  0
 28 29  2  0
  2  7  2  0
 29 30  1  0
 13 15  1  6
 30 31  2  0
 31 26  1  0
  1  3  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2063867

   Me-Ala-Chg-Pro-NHBn(4-Cl)

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: 463.02

Molecular Weight (Monoisotopic): 462.2398

AlogP: 2.62

#Rotatable Bonds: 8

Polar Surface Area: 90.54

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.53

CX Basic pKa: 8.60

CX LogP: 2.56

CX LogD: 1.33

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -0.77

References

1. Flygare JA, Beresini M, Budha N, Chan H, Chan IT, Cheeti S, Cohen F, Deshayes K, Doerner K, Eckhardt SG, Elliott LO, Feng B, Franklin MC, Reisner SF, Gazzard L, Halladay J, Hymowitz SG, La H, LoRusso P, Maurer B, Murray L, Plise E, Quan C, Stephan JP, Young SG, Tom J, Tsui V, Um J, Varfolomeev E, Vucic D, Wagner AJ, Wallweber HJ, Wang L, Ware J, Wen Z, Wong H, Wong JM, Wong M, Wong S, Yu R, Zobel K, Fairbrother WJ..  (2012)  Discovery of a potent small-molecule antagonist of inhibitor of apoptosis (IAP) proteins and clinical candidate for the treatment of cancer (GDC-0152).,  55  (9): [PMID:22413863] [10.1021/jm300060k]

Source

Source(1):

• Scientific Literature