The store will not work correctly when cookies are disabled.
JavaScript seems to be disabled in your browser. For the best experience on our site, be sure to turn on Javascript in your browser.
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:
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 Associated Targets(Human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 459.91Molecular Weight (Monoisotopic): 459.1473AlogP: 2.43#Rotatable Bonds: 5Polar 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: 2.24Aromatic 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 ]