5-(3-(4-(2-chlorophenyl)piperazin-1-yl)-3-oxopropyl)imidazolidine-2,4-dione

ID: ALA4877395

PubChem CID: 22107960

Max Phase: Preclinical

Molecular Formula: C16H19ClN4O3

Molecular Weight: 350.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C(CCC(=O)N2CCN(c3ccccc3Cl)CC2)N1

Standard InChI:  InChI=1S/C16H19ClN4O3/c17-11-3-1-2-4-13(11)20-7-9-21(10-8-20)14(22)6-5-12-15(23)19-16(24)18-12/h1-4,12H,5-10H2,(H2,18,19,23,24)

Standard InChI Key:  BSPSHXHBYJRBIT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   10.8215   -4.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4129   -4.0320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9607   -3.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7080   -3.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6198   -4.5703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4871   -5.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7899   -2.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4130   -3.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1220   -3.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8270   -3.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8270   -2.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5361   -3.7558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2452   -3.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9502   -3.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9502   -4.5730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2452   -4.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5361   -4.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6592   -4.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3683   -4.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0733   -4.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0733   -5.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3683   -6.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6592   -5.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3694   -3.7558    0.0000 Cl  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
 10 11  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 17  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 15 18  1  0
 10 12  1  0
  4  8  1  0
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877395

   5-[3-[4-(2-Chlorophenyl)piperazin-1-yl]-3-oxopropyl]imidazolidine-2,4-dione

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: 350.81

Molecular Weight (Monoisotopic): 350.1146

AlogP: 0.98

#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: 8.64

CX Basic pKa: 0.39

CX LogP: 0.75

CX LogD: 0.72

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: -1.33

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