ID: ALA254370
Chembl Id: CHEMBL254370
PubChem CID: 10200589
Max Phase: Preclinical
Molecular Formula: C22H23N3O4
Molecular Weight: 393.44
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: CC[C@@H](Nc1c(Nc2cccc(C(=O)N(C)C)c2O)c(=O)c1=O)c1ccccc1
Standard InChI: InChI=1S/C22H23N3O4/c1-4-15(13-9-6-5-7-10-13)23-17-18(21(28)20(17)27)24-16-12-8-11-14(19(16)26)22(29)25(2)3/h5-12,15,23-24,26H,4H2,1-3H3/t15-/m1/s1
Standard InChI Key: ILEJORXRDPNPIM-OAHLLOKOSA-N
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| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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| Molecular Weight: 393.44 | Molecular Weight (Monoisotopic): 393.1689 | AlogP: 3.00 | #Rotatable Bonds: 7 |
| Polar Surface Area: 98.74 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 3 |
| #RO5 Violations: ┄ | HBA (Lipinski): 7 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: 8.06 | CX Basic pKa: ┄ | CX LogP: 3.30 | CX LogD: 3.22 |
| Aromatic Rings: 3 | Heavy Atoms: 29 | QED Weighted: 0.42 | Np Likeness Score: -0.82 |
| 1. Dwyer MP, Yu Y, Chao J, Aki C, Chao J, Biju P, Girijavallabhan V, Rindgen D, Bond R, Mayer-Ezel R, Jakway J, Hipkin RW, Fossetta J, Gonsiorek W, Bian H, Fan X, Terminelli C, Fine J, Lundell D, Merritt JR, Rokosz LL, Kaiser B, Li G, Wang W, Stauffer T, Ozgur L, Baldwin J, Taveras AG.. (2006) Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5- methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123): a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist., 49 (26): [PMID:17181143] [10.1021/jm0609622] |
| 2. Lai G, Merritt JR, He Z, Feng D, Chao J, Czarniecki MF, Rokosz LL, Stauffer TM, Rindgen D, Taveras AG.. (2008) Synthesis and structure-activity relationships of new disubstituted phenyl-containing 3,4-diamino-3-cyclobutene-1,2-diones as CXCR2 receptor antagonists., 18 (6): [PMID:18304809] [10.1016/j.bmcl.2008.02.010] |
| 3. Biju P, Taveras AG, Dwyer MP, Yu Y, Chao J, Hipkin RW, Fan X, Rindgen D, Fine J, Lundell D.. (2009) Fluoroalkyl alpha side chain containing 3,4-diamino-cyclobutenediones as potent and orally bioavailable CXCR2-CXCR1 dual antagonists., 19 (5): [PMID:19196511] [10.1016/j.bmcl.2009.01.033] |
| 4. Aki C, Chao J, Ferreira JA, Dwyer MP, Yu Y, Chao J, Merritt RJ, Lai G, Wu M, Hipkin RW, Fan X, Gonsiorek W, Fosseta J, Rindgen D, Fine J, Lundell D, Taveras AG, Biju P.. (2009) Diaminocyclobutenediones as potent and orally bioavailable CXCR2 receptor antagonists: SAR in the phenolic amide region., 19 (15): [PMID:19525110] [10.1016/j.bmcl.2009.05.049] |
| 5. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds, [10.6019/CHEMBL3301361] |
| 6. Chasák J, Šlachtová V, Urban M, Brulíková L.. (2021) Squaric acid analogues in medicinal chemistry., 209 [PMID:33035923] [10.1016/j.ejmech.2020.112872] |
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