5-methyl-5-(3-(3-methyl-4-phenylpiperazin-1-yl)-3-oxopropyl)imidazolidine-2,4-dione

ID: ALA4871605

PubChem CID: 121437823

Max Phase: Preclinical

Molecular Formula: C18H24N4O3

Molecular Weight: 344.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1CN(C(=O)CCC2(C)NC(=O)NC2=O)CCN1c1ccccc1

Standard InChI:  InChI=1S/C18H24N4O3/c1-13-12-21(10-11-22(13)14-6-4-3-5-7-14)15(23)8-9-18(2)16(24)19-17(25)20-18/h3-7,13H,8-12H2,1-2H3,(H2,19,20,24,25)

Standard InChI Key:  BIKHSLFTWKBHHX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   10.5175   -9.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7339   -9.5528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7339   -8.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5175   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0016   -9.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7701  -10.5932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0652   -8.2448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2282   -8.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9431   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6580   -8.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3687   -8.4763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0836   -8.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7985   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7985   -9.3002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0836   -9.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3687   -9.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5092   -9.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2241   -9.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9389   -9.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9389  -10.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2241  -10.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5092  -10.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6580   -7.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1803   -7.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5127   -8.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  1  6  2  0
  3  7  2  0
  8  9  1  0
  9 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 16  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 14 17  1  0
 10 11  1  0
 10 23  2  0
  4  8  1  0
  4 24  1  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871605

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 344.42

Molecular Weight (Monoisotopic): 344.1848

AlogP: 1.10

#Rotatable Bonds: 4

Polar Surface Area: 81.75

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.90

CX Basic pKa: 3.43

CX LogP: 0.99

CX LogD: 0.98

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: -1.05

References

1. 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(1):

• Scientific Literature