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

ID: ALA4878680

PubChem CID: 17505126

Max Phase: Preclinical

Molecular Formula: C17H22N4O4

Molecular Weight: 346.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(C(=O)CCC2NC(=O)NC2=O)CC1

Standard InChI:  InChI=1S/C17H22N4O4/c1-25-14-5-3-2-4-13(14)20-8-10-21(11-9-20)15(22)7-6-12-16(23)19-17(24)18-12/h2-5,12H,6-11H2,1H3,(H2,18,19,23,24)

Standard InChI Key:  MXXDNXVZZLLILP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   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
   17.3735   -3.7529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6663   -3.3435    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
 24 25  1  0
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878680

   5-[3-[4-(2-Methoxyphenyl)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: 346.39

Molecular Weight (Monoisotopic): 346.1641

AlogP: 0.33

#Rotatable Bonds: 5

Polar Surface Area: 90.98

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: 2.22

CX LogP: -0.01

CX LogD: -0.04

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -1.08

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