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

ID: ALA4846457

PubChem CID: 121437747

Max Phase: Preclinical

Molecular Formula: C18H22Cl2N4O4

Molecular Weight: 429.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(CC(CO)C(=O)N2CCN(c3cc(Cl)cc(Cl)c3)CC2)NC(=O)NC1=O

Standard InChI:  InChI=1S/C18H22Cl2N4O4/c1-18(16(27)21-17(28)22-18)9-11(10-25)15(26)24-4-2-23(3-5-24)14-7-12(19)6-13(20)8-14/h6-8,11,25H,2-5,9-10H2,1H3,(H2,21,22,27,28)

Standard InChI Key:  LHKXLEZLEFHFJV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    9.6688  -10.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8877  -10.1627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8954   -9.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6839   -9.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1590   -9.7643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9146  -11.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2327   -8.8474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3529   -8.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4015   -8.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1115   -9.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8292   -8.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8369   -7.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5392   -9.1205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2568   -8.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9711   -9.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9633   -9.9579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2414  -10.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5314   -9.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6732  -10.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3910   -9.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1010  -10.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0932  -11.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3755  -11.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6655  -11.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3678  -12.4454    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.8186   -9.9866    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1043   -9.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8152  -10.3480    0.0000 O   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
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4846457

   ---

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: 429.30

Molecular Weight (Monoisotopic): 428.1018

AlogP: 1.24

#Rotatable Bonds: 5

Polar Surface Area: 101.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.90

CX Basic pKa: 0.12

CX LogP: 1.05

CX LogD: 1.03

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.82

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