rac-5-(3-(4-(3,5-dichlorophenyl)piperazin-1-yl)-2-methyl-3-oxopropyl)-5-methylimidazolidine-2,4-dione

ID: ALA4856943

PubChem CID: 121437795

Max Phase: Preclinical

Molecular Formula: C18H22Cl2N4O3

Molecular Weight: 413.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(CC1(C)NC(=O)NC1=O)C(=O)N1CCN(c2cc(Cl)cc(Cl)c2)CC1

Standard InChI:  InChI=1S/C18H22Cl2N4O3/c1-11(10-18(2)16(26)21-17(27)22-18)15(25)24-5-3-23(4-6-24)14-8-12(19)7-13(20)9-14/h7-9,11H,3-6,10H2,1-2H3,(H2,21,22,26,27)

Standard InChI Key:  KTSVBNSBXWVDTE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    9.8263  -10.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454  -10.1619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0530   -9.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8414   -9.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3165   -9.7635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0721  -11.2145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3904   -8.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5105   -8.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5590   -8.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2690   -9.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9866   -8.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9943   -7.8720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6965   -9.1198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4141   -8.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1282   -9.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1206   -9.9571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3987  -10.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6888   -9.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8304  -10.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5481   -9.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2581  -10.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2503  -11.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5326  -11.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8227  -11.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5249  -12.4444    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.9757   -9.9858    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2617   -9.9284    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
  4  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 23 25  1  0
 21 26  1  0
 16 19  1  0
 11 13  1  0
  4  9  1  0
 10 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4856943

   ---

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: 413.31

Molecular Weight (Monoisotopic): 412.1069

AlogP: 2.27

#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: 0.18

CX LogP: 2.33

CX LogD: 2.31

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: -1.06

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