US9206139, 3

ID: ALA3980860

PubChem CID: 74221072

Max Phase: Preclinical

Molecular Formula: C20H22F3N3O3

Molecular Weight: 409.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)[C@](CNC(=O)[C@@H](Cc2ccc(C(F)(F)F)cc2)C2CC2)(C2CC2)N1

Standard InChI:  InChI=1S/C20H22F3N3O3/c21-20(22,23)14-5-1-11(2-6-14)9-15(12-3-4-12)16(27)24-10-19(13-7-8-13)17(28)25-18(29)26-19/h1-2,5-6,12-13,15H,3-4,7-10H2,(H,24,27)(H2,25,26,28,29)/t15-,19-/m0/s1

Standard InChI Key:  JHOUEQAOHDTLPY-KXBFYZLASA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    3.6384   -0.9011    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -2.7004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377   -2.1009    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -0.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6427   -1.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1427   -1.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024    2.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8842   -0.0797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3454   -1.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6385   -2.4767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8454   -1.5094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3112   -0.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4464    0.3055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4004    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8212    1.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0711    2.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
 10  9  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 11  1  0
 10 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 18 17  1  1
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 18  1  0
 23 24  2  0
 18 25  1  0
 25 26  1  0
 26 27  1  0
 27 25  1  0
  8 28  1  0
 28 29  2  0
 29  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980860

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

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: 409.41

Molecular Weight (Monoisotopic): 409.1613

AlogP: 2.38

#Rotatable Bonds: 7

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: 2.61

CX LogD: 2.59

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -0.46

References

1.  (2015)  Aggrecanase inhibitors, 

2. 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]

3. Brebion F, Gosmini R, Deprez P, Varin M, Peixoto C, Alvey L, Jary H, Bienvenu N, Triballeau N, Blanque R, Cottereaux C, Christophe T, Vandervoort N, Mollat P, Touitou R, Leonard P, De Ceuninck F, Botez I, Monjardet A, van der Aar E, Amantini D..  (2021)  Discovery of GLPG1972/S201086, a Potent, Selective, and Orally Bioavailable ADAMTS-5 Inhibitor for the Treatment of Osteoarthritis.,  64  (6.0): [PMID:33719441] [10.1021/acs.jmedchem.0c02008]

Source

Source(2):

• Scientific Literature
• BindingDB Database