US8785477, 8

ID: ALA3665964

PubChem CID: 76167613

Max Phase: Preclinical

Molecular Formula: C20H25F4N3O2

Molecular Weight: 415.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(F)C(=O)N1CC2CCN(C(=O)CC(N)Cc3cc(F)c(F)cc3F)C2C1

Standard InChI:  InChI=1S/C20H25F4N3O2/c1-20(2,24)19(29)26-9-11-3-4-27(17(11)10-26)18(28)7-13(25)5-12-6-15(22)16(23)8-14(12)21/h6,8,11,13,17H,3-5,7,9-10,25H2,1-2H3

Standard InChI Key:  HQQONCVLYGCKBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.1779   -3.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0157   -3.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5255   -4.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191   -4.5887    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6281   -2.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8218   -2.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4623    2.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623    2.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258    1.2743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515    0.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024   -0.3599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9659    1.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3940    1.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6449    0.1838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5084    2.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9364    1.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2477    0.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6741   -0.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9230   -1.2045    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7893    0.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9304    0.6013    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4781    2.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0517    2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8028    4.0781    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
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 14  7  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 21  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3665964

   3-Amino-1-[5-(2-fluoro-2-methylpropanoyl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-1-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

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: 415.43

Molecular Weight (Monoisotopic): 415.1883

AlogP: 2.17

#Rotatable Bonds: 5

Polar Surface Area: 66.64

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.78

CX LogP: 1.51

CX LogD: 0.11

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -0.76

References

1.  (2014)  Hexahydropyrrolo[3,4-b]pyrrole derivatives, preparation methods and pharmaceutical uses thereof, 

Source

Source(1):

• BindingDB Database