(S)-5,5-dimethyl-3-[(S)-2,2,2-trifluoro-1-(4'-methanesulfonyl-biphenyl-4-yl)-ethylamino]-dihydro-furan-2-one

ID: ALA400725

PubChem CID: 44447644

Max Phase: Preclinical

Molecular Formula: C21H22F3NO4S

Molecular Weight: 441.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C[C@H](N[C@@H](c2ccc(-c3ccc(S(C)(=O)=O)cc3)cc2)C(F)(F)F)C(=O)O1

Standard InChI:  InChI=1S/C21H22F3NO4S/c1-20(2)12-17(19(26)29-20)25-18(21(22,23)24)15-6-4-13(5-7-15)14-8-10-16(11-9-14)30(3,27)28/h4-11,17-18,25H,12H2,1-3H3/t17-,18-/m0/s1

Standard InChI Key:  MELICPULJWKHGK-ROUUACIJSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
   10.7406  -18.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7395  -19.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4494  -20.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1692  -19.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1663  -18.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4476  -18.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0236  -20.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3150  -19.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5996  -20.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5981  -21.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3175  -21.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0261  -21.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8868  -21.4267    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1669  -21.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2937  -22.1437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4772  -20.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8757  -18.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5929  -18.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8720  -17.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8648  -16.8910    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6955  -17.7105    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0486  -17.7228    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3067  -18.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0905  -18.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5805  -18.1236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0989  -17.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3114  -17.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8094  -16.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8937  -17.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3404  -19.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3007  -19.3489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  2  0
  3  4  2  0
 13 16  2  0
  7  8  2  0
  5 17  1  0
 17 18  1  0
  8  9  1  0
 17 19  1  1
  4  5  1  0
 19 20  1  0
  9 10  2  0
 19 21  1  0
  2  3  1  0
 19 22  1  0
 10 11  1  0
 18 23  1  0
 23 24  1  0
  5  6  2  0
 11 12  2  0
 12  7  1  0
  6  1  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 10 13  1  0
 26 28  1  0
  1  2  2  0
 26 29  1  0
 13 14  1  0
 24 30  2  0
  2  7  1  0
 23 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA400725

   (3S)-5,5-dimethyl-3-[[(1S)-2,2,2-trifluoro-1-[4-(4-methylsulfonylphenyl)phenyl]ethyl]amino]oxolan-2-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: 441.47

Molecular Weight (Monoisotopic): 441.1222

AlogP: 4.04

#Rotatable Bonds: 5

Polar Surface Area: 72.47

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.89

CX LogP: 3.46

CX LogD: 3.46

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.71

Np Likeness Score: -0.46

References

1. Gauthier JY, Chauret N, Cromlish W, Desmarais S, Duong LT, Falgueyret JP, Kimmel DB, Lamontagne S, Léger S, LeRiche T, Li CS, Massé F, McKay DJ, Nicoll-Griffith DA, Oballa RM, Palmer JT, Percival MD, Riendeau D, Robichaud J, Rodan GA, Rodan SB, Seto C, Thérien M, Truong VL, Venuti MC, Wesolowski G, Young RN, Zamboni R, Black WC..  (2008)  The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K.,  18  (3): [PMID:18226527] [10.1016/j.bmcl.2007.12.047]

Source

Source(1):

• Scientific Literature