US9422333, I-1

ID: ALA3921185

PubChem CID: 59191926

Max Phase: Preclinical

Molecular Formula: C27H42N6O6

Molecular Weight: 546.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)NC[C@H](NC(=O)NC(C)(C)C)C(=O)N1CC2[C@@H]([C@H]1C(=O)NC(CC1CCC1)C(=O)C(N)=O)C2(C)C

Standard InChI:  InChI=1S/C27H42N6O6/c1-7-18(34)29-12-17(31-25(39)32-26(2,3)4)24(38)33-13-15-19(27(15,5)6)20(33)23(37)30-16(21(35)22(28)36)11-14-9-8-10-14/h7,14-17,19-20H,1,8-13H2,2-6H3,(H2,28,36)(H,29,34)(H,30,37)(H2,31,32,39)/t15?,16?,17-,19-,20-/m0/s1

Standard InChI Key:  SWJQTCTXGIEKDV-ZFHYAEIBSA-N

Molfile:  

     RDKit          2D

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    8.0377    0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2289   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7364   -0.7126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0102   -3.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3873   -4.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1470   -3.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1255   -2.0835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102   -3.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5026   -3.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3873   -4.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8384   -4.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6038   -6.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4050   -4.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2120   -4.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2910   -5.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8071   -6.9788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4840   -5.7511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3664    1.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612    1.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914    2.9827    0.0000 C   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  1  0
  6  7  2  0
  6  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  6
 21 22  1  0
 22 18  1  0
 22 23  1  6
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 28  1  0
 26 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  2  0
 34 36  1  0
 21 37  1  0
 37 20  1  0
 37 38  1  0
 37 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3921185

   (1R,2S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[(2S)-2-(tert-butylcarbamoylamino)-3-(prop-2-enoylamino)propanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

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: 546.67

Molecular Weight (Monoisotopic): 546.3166

AlogP: -0.03

#Rotatable Bonds: 11

Polar Surface Area: 179.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.27

CX Basic pKa: ┄

CX LogP: -0.07

CX LogD: -0.07

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.18

Np Likeness Score: 0.11

References

1.  (2016)  HCV protease inhibitors and uses thereof, 

Source

Source(1):

• BindingDB Database