(1R,2S,5S)-N-((2R,3R)-4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

ID: ALA3542247

PubChem CID: 118753404

Max Phase: Preclinical

Molecular Formula: C27H47N5O5

Molecular Weight: 521.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)N[C@H](C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)N[C@H](CC1CCC1)[C@@H](O)C(N)=O)C2(C)C)C(C)(C)C

Standard InChI:  InChI=1S/C27H47N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-20,33H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16+,17-,18-,19+,20+/m0/s1

Standard InChI Key:  FEBWCINGHXXUCV-GNVSMLMZSA-N

Molfile:  

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
   31.6645   -8.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0788   -7.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2538   -7.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9497  -11.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6642  -11.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3787  -11.7001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6642  -10.4626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3296   -9.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9955   -9.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0496  -10.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0608  -11.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7583   -9.9593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2503   -9.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0752   -9.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7835   -8.7793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.6627   -8.6042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.2353  -11.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9497  -12.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2353  -10.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5208  -11.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5169  -10.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2353  -12.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2353  -13.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5208  -12.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5208  -14.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5208  -15.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8063  -13.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8002  -14.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4784  -10.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1872   -9.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9072  -10.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9185  -11.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.6160   -9.9204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1760   -9.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4897  -11.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0771  -11.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0832  -12.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9081  -12.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9008  -11.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8 14  1  0
 13  9  1  0
  9  7  1  0
  8 10  1  1
 10 11  2  0
 10 12  1  0
 14 13  1  0
  1 14  1  0
 13  1  1  0
 14 15  1  1
 13 16  1  1
  4 17  1  1
  4 18  1  0
 17 19  1  0
 17 20  1  0
 17 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 12 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 30 34  1  1
 29 35  1  1
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3542247

   ---

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: 521.70

Molecular Weight (Monoisotopic): 521.3577

AlogP: 1.50

#Rotatable Bonds: 8

Polar Surface Area: 153.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.54

CX Basic pKa: ┄

CX LogP: 0.86

CX LogD: 0.86

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.33

Np Likeness Score: 0.32

References

1. Ghosal A, Yuan Y, Tong W, Su AD, Gu C, Chowdhury SK, Kishnani NS, Alton KB..  (2011)  Characterization of human liver enzymes involved in the biotransformation of boceprevir, a hepatitis C virus protease inhibitor.,  39  (3): [PMID:21123164] [10.1124/dmd.110.036996]

Source

Source(1):

• Scientific Literature