5-((2S)-2-(2-(3-chloro-2-fluorophenyl)-1-hydroxy-4-methyl-1H-imidazole-5-carboxamido)-3-(4-(cyclopropanecarboxamido)phenyl)propanamido)-1H-indole-2-carboxylic acid

ID: ALA4856139

PubChem CID: 164609734

Max Phase: Preclinical

Molecular Formula: C33H28ClFN6O6

Molecular Weight: 659.07

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(-c2cccc(Cl)c2F)n(O)c1C(=O)N[C@@H](Cc1ccc(NC(=O)C2CC2)cc1)C(=O)Nc1ccc2[nH]c(C(=O)O)cc2c1

Standard InChI:  InChI=1S/C33H28ClFN6O6/c1-16-28(41(47)29(36-16)22-3-2-4-23(34)27(22)35)32(44)40-25(13-17-5-9-20(10-6-17)37-30(42)18-7-8-18)31(43)38-21-11-12-24-19(14-21)15-26(39-24)33(45)46/h2-6,9-12,14-15,18,25,39,47H,7-8,13H2,1H3,(H,37,42)(H,38,43)(H,40,44)(H,45,46)/t25-/m0/s1

Standard InChI Key:  SXGKAPMKNHSXRE-VWLOTQADSA-N

Molfile:  

 
     RDKit          2D

 47 52  0  0  0  0  0  0  0  0999 V2000
   23.3890   -4.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0967   -3.9580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8044   -4.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8019   -5.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5088   -5.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5074   -3.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6813   -3.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9736   -4.3666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2659   -3.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3890   -5.1838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6813   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3890   -2.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0963   -3.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8035   -2.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8039   -1.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0912   -1.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3869   -1.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2659   -3.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5582   -4.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8103   -4.0386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2635   -4.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6721   -5.3536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4714   -5.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0784   -5.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4555   -4.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1239   -3.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3120   -3.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8308   -4.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1673   -5.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9783   -5.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6382   -3.2397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6893   -5.8027    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.3127   -5.9676    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.2148   -4.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2184   -5.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9994   -5.4332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4785   -4.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9935   -4.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2957   -4.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7074   -5.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7011   -4.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5111   -1.5082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2193   -1.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9265   -1.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2204   -2.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7432   -1.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3336   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 35  2  0
 34  6  2  0
  6  3  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  1 10  2  0
  7 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 18  2  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
 23 24  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 21 25  1  0
 20 31  1  0
 29 32  1  0
 30 33  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 34  1  0
 37 39  1  0
 39 40  2  0
 39 41  1  0
 15 42  1  0
 42 43  1  0
 43 44  1  0
 43 45  2  0
 46 44  1  0
 47 46  1  0
 44 47  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4856139

   ---

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: 659.07

Molecular Weight (Monoisotopic): 658.1743

AlogP: 5.40

#Rotatable Bonds: 10

Polar Surface Area: 178.44

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 3.60

CX Basic pKa: 2.35

CX LogP: 3.72

CX LogD: 0.56

Aromatic Rings: 5

Heavy Atoms: 47

QED Weighted: 0.11

Np Likeness Score: -1.22

References

1. Lei Y, Zhang B, Zhang Y, Dai X, Duan Y, Mao Q, Gao J, Yang Y, Bao Z, Fu X, Ping K, Yan C, Mou Y, Wang S..  (2021)  Design, synthesis and biological evaluation of novel FXIa inhibitors with 2-phenyl-1H-imidazole-5-carboxamide moiety as P1 fragment.,  220  [PMID:33894565] [10.1016/j.ejmech.2021.113437]

Source

Source(1):

• Scientific Literature