(S)-N-(((R)-4-Cyclopropyl-2,5-dioxoimidazolidin-4-yl)methyl)-2-methyl-3-(4-(trifluoromethyl)phenyl)propanamide

ID: ALA4094455

PubChem CID: 137652598

Max Phase: Preclinical

Molecular Formula: C18H20F3N3O3

Molecular Weight: 383.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](Cc1ccc(C(F)(F)F)cc1)C(=O)NC[C@@]1(C2CC2)NC(=O)NC1=O

Standard InChI:  InChI=1S/C18H20F3N3O3/c1-10(8-11-2-4-13(5-3-11)18(19,20)21)14(25)22-9-17(12-6-7-12)15(26)23-16(27)24-17/h2-5,10,12H,6-9H2,1H3,(H,22,25)(H2,23,24,26,27)/t10-,17-/m0/s1

Standard InChI Key:  NPTUUUXCZCQNQS-BTDLBPIBSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    8.8348   -4.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3971   -5.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1971   -5.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0869   -3.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0297   -4.8586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7769   -5.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5708   -7.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2365   -6.6062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9709   -5.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1468   -5.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8991   -6.6146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6552   -5.1630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5715   -7.9195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8781   -5.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2117   -4.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3884   -4.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7556   -5.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5066   -6.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0643   -7.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8705   -6.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1158   -6.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5565   -5.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4298   -7.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1841   -8.3248    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.2347   -7.3561    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.0100   -8.1202    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.1506   -6.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  1  5  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 11  1  0
 10 12  2  0
  7 13  2  0
 14 15  1  0
 15 16  1  0
 14 16  1  0
  9 14  1  0
  9  6  1  1
  5  6  1  0
  3 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
 20 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  2 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4094455

   ---

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: 383.37

Molecular Weight (Monoisotopic): 383.1457

AlogP: 1.99

#Rotatable Bonds: 6

Polar Surface Area: 87.30

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.88

CX Basic pKa: ┄

CX LogP: 2.34

CX LogD: 2.33

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -0.73

References

1. Durham TB, Marimuthu J, Toth JL, Liu C, Adams L, Mudra DR, Swearingen C, Lin C, Chambers MG, Thirunavukkarasu K, Wiley MR..  (2017)  A Highly Selective Hydantoin Inhibitor of Aggrecanase-1 and Aggrecanase-2 with a Low Projected Human Dose.,  60  (13): [PMID:28613895] [10.1021/acs.jmedchem.7b00650]

Source

Source(1):

• Scientific Literature