5-(3-oxo-3-(4-(pyridin-3-yl)piperazin-1-yl)propyl)imidazolidine-2,4-dione

ID: ALA4871267

PubChem CID: 70736756

Max Phase: Preclinical

Molecular Formula: C15H19N5O3

Molecular Weight: 317.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C(CCC(=O)N2CCN(c3cccnc3)CC2)N1

Standard InChI:  InChI=1S/C15H19N5O3/c21-13(4-3-12-14(22)18-15(23)17-12)20-8-6-19(7-9-20)11-2-1-5-16-10-11/h1-2,5,10,12H,3-4,6-9H2,(H2,17,18,22,23)

Standard InChI Key:  MOCDMUMSDFCTSR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  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 N   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
  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
M  END

Alternative Forms

1. Parent:

   

   ALA4871267

   5-{3-Oxo-3-[4-(3-pyridinyl)-1-piperazinyl]propyl}-2,4-imidazolidinedione

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: 317.35

Molecular Weight (Monoisotopic): 317.1488

AlogP: -0.28

#Rotatable Bonds: 4

Polar Surface Area: 94.64

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.64

CX Basic pKa: 5.57

CX LogP: -1.07

CX LogD: -1.10

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -1.39

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