US8552202, Compound 2

ID: ALA3648397

PubChem CID: 58101953

Max Phase: Preclinical

Molecular Formula: C21H25FN2O4

Molecular Weight: 388.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H](C(=O)N1C[C@H](F)[C@H]2OCC(=O)[C@H]21)C1CCCCC1)c1ccccc1

Standard InChI:  InChI=1S/C21H25FN2O4/c22-15-11-24(18-16(25)12-28-19(15)18)21(27)17(13-7-3-1-4-8-13)23-20(26)14-9-5-2-6-10-14/h2,5-6,9-10,13,15,17-19H,1,3-4,7-8,11-12H2,(H,23,26)/t15-,17-,18+,19+/m0/s1

Standard InChI Key:  KKKHMKQUVHHTJX-GDAAHCPNSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
    1.4553   -2.0031    0.0000 F   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
    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 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
   -1.9615   -1.9133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7115    0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4167    1.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351    3.3760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    5.0236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6079    5.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460    5.1703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110    7.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9100    8.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101    9.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111   10.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120    9.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    8.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6023    2.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    3.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2005    2.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958    1.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8944    0.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977    1.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  2  1  0
  6  7  1  1
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  1
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 13 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3648397

   N-[(1S)-2-[(3aS,6S,6aS)-6-fluoro-3-oxo-3a,5,6,6a-tetrahydrofuro[3,2-b]pyrrol-4-yl]-1-cyclohexyl-2-oxoethyl]benzamide

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: 388.44

Molecular Weight (Monoisotopic): 388.1798

AlogP: 1.88

#Rotatable Bonds: 4

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.32

CX LogD: 2.32

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.85

Np Likeness Score: -0.14

References

1.  (2013)  Furo[3, 2-B] pyrrol-3-ones as cathespin S inhibitors, 

Source

Source(1):

• BindingDB Database