5-(3-((S)-4-(3-chloro-4-fluorophenyl)-3-methylpiperazin-1-yl)-3-oxopropyl)-5-(pyridin-2-yl)imidazolidine-2,4-dione

ID: ALA4876618

PubChem CID: 121437712

Max Phase: Preclinical

Molecular Formula: C22H23ClFN5O3

Molecular Weight: 459.91

Molecule Type: Unknown

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  C[C@H]1CN(C(=O)CCC2(c3ccccn3)NC(=O)NC2=O)CCN1c1ccc(F)c(Cl)c1

Standard InChI:  InChI=1S/C22H23ClFN5O3/c1-14-13-28(10-11-29(14)15-5-6-17(24)16(23)12-15)19(30)7-8-22(18-4-2-3-9-25-18)20(31)26-21(32)27-22/h2-6,9,12,14H,7-8,10-11,13H2,1H3,(H2,26,27,31,32)/t14-,22?/m0/s1

Standard InChI Key:  WECKJJDCDPVTTO-XLEXHMCLSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    9.4482   -7.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2295   -7.6214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7238   -8.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2442   -8.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4557   -8.7107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7757   -7.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5491   -8.2770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9129   -9.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9619   -9.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9693  -10.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6871  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6946  -11.4210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3974  -10.1771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3899   -9.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1044   -8.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8222   -9.3400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8296  -10.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1193  -10.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5325   -8.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5250   -8.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2353   -7.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9531   -8.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9606   -8.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2503   -9.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2278   -6.8483    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.6643   -7.6616    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957   -9.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7645  -10.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2531  -11.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0767  -11.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4042  -10.3749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0985   -8.1080    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
  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
 21 25  1  0
 16 19  1  0
 11 13  1  0
  4  9  1  0
 22 26  1  0
  8 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31  8  1  0
 15 32  1  6
M  END

Alternative Forms

  1. Parent:

    ALA4876618

    ---

Associated Targets(Human)

ADAMTS5 Tchem ADAMTS5 (711 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADAMTS1 Tchem ADAMTS1 (32 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADAMTS4 Tchem ADAMTS4 (425 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP2 Tchem Matrix metalloproteinase-2 (6627 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADAM17 Tchem ADAM17 (3550 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 459.91Molecular Weight (Monoisotopic): 459.1473AlogP: 2.43#Rotatable Bonds: 5
Polar Surface Area: 94.64Molecular Species: NEUTRALHBA: 5HBD: 2
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 8.52CX Basic pKa: 3.69CX LogP: 2.28CX LogD: 2.24
Aromatic Rings: 2Heavy Atoms: 32QED Weighted: 0.67Np Likeness Score: -1.61

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