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AGG-523
ID: ALA4859268
Max Phase: Phase
Molecular Formula: C28H29FN2O4
Molecular Weight: 476.55
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (4): Agg-523 | PF-05212371 | PF-5212371 | WAY-266523
Synonyms from Alternative Forms(4):
Canonical SMILES: CC(C)(Cc1ccc(F)cc1)NC(=O)[C@H](CCC(=O)O)NC(=O)c1ccc(-c2ccccc2)cc1
Standard InChI: InChI=1S/C28H29FN2O4/c1-28(2,18-19-8-14-23(29)15-9-19)31-27(35)24(16-17-25(32)33)30-26(34)22-12-10-21(11-13-22)20-6-4-3-5-7-20/h3-15,24H,16-18H2,1-2H3,(H,30,34)(H,31,35)(H,32,33)/t24-/m0/s1
Standard InChI Key: JWQMTWCFNZSLNR-DEOSSOPVSA-N
Associated Targets(Human)
ADAMTS5 Tchem ADAMTS5 (711 Activities)
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
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ADAMTS4 Tchem ADAMTS4 (425 Activities)
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MMP13 Tchem Matrix metalloproteinase 13 (4133 Activities)
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MMP12 Tchem Matrix metalloproteinase 12 (1130 Activities)
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MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)
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MMP2 Tchem Matrix metalloproteinase-2 (6627 Activities)
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MMP8 Tchem Matrix metalloproteinase 8 (1942 Activities)
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MMP14 Tchem Matrix metalloproteinase 14 (1592 Activities)
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Associated Targets(non-human)
Liver microsomes (8692 Activities)
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: Yes | Availability: No | Prodrug: 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 |
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Properties
| Molecular Weight: 476.55 | Molecular Weight (Monoisotopic): 476.2111 | AlogP: 4.59 | #Rotatable Bonds: 10 |
| Polar Surface Area: 95.50 | Molecular Species: ACID | HBA: 3 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 4.25 | CX Basic pKa: | CX LogP: 4.66 | CX LogD: 1.66 |
| Aromatic Rings: 3 | Heavy Atoms: 35 | QED Weighted: 0.40 | Np Likeness Score: -0.60 |
References
| 1. Gilbert AM, Bursavich MG, Lombardi S, Georgiadis KE, Reifenberg E, Flannery CR, Morris EA.. (2008) N-((8-hydroxy-5-substituted-quinolin-7-yl)(phenyl)methyl)-2-phenyloxy/amino-acetamide inhibitors of ADAMTS-5 (Aggrecanase-2)., 18 (24): [PMID:18974001] [10.1016/j.bmcl.2008.10.065] |
| 2. Unpublished dataset, |
| 3. 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] |
| 4. Cuffaro D, Ciccone L, Rossello A, Nuti E, Santamaria S.. (2022) Targeting Aggrecanases for Osteoarthritis Therapy: From Zinc Chelation to Exosite Inhibition., 65 (20.0): [PMID:36250680] [10.1021/acs.jmedchem.2c01177] |
Source
Source(2):