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

ID: ALA4850670

PubChem CID: 42909982

Max Phase: Preclinical

Molecular Formula: C16H20N4O3

Molecular Weight: 316.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C(CCC(=O)N2CCN(c3ccccc3)CC2)N1

Standard InChI:  InChI=1S/C16H20N4O3/c21-14(7-6-13-15(22)18-16(23)17-13)20-10-8-19(9-11-20)12-4-2-1-3-5-12/h1-5,13H,6-11H2,(H2,17,18,22,23)

Standard InChI Key:  GYKPTYVBUHPMNZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.0428   -5.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342   -4.7088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -4.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9294   -4.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8412   -5.2472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -6.1611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113   -3.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6343   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3434   -4.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484   -3.2069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7575   -4.4326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4666   -4.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1715   -4.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1715   -5.2498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4666   -5.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7575   -5.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8806   -5.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5897   -5.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2947   -5.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2947   -6.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5897   -6.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8806   -6.4756    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:

   

   ALA4850670

   5-[3-Oxo-3-(4-phenylpiperazin-1-yl)propyl]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: 316.36

Molecular Weight (Monoisotopic): 316.1535

AlogP: 0.32

#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: 3.43

CX LogP: 0.14

CX LogD: 0.12

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: -1.16

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