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ID: ALA47028
Max Phase: Preclinical
Molecular Formula: C18H20F2N4O3
Molecular Weight: 378.38
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CN1CCN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)CC1
Standard InChI: InChI=1S/C18H20F2N4O3/c1-22-4-6-23(7-5-22)16-12(19)14(21)11-15(13(16)20)24(9-2-3-9)8-10(17(11)25)18(26)27/h8-9H,2-7,21H2,1H3,(H,26,27)
Standard InChI Key: VSPMPXLOUWFGBD-UHFFFAOYSA-N
Associated Targets(non-human)
gyrB DNA gyrase (2092 Activities)
Escherichia coli (133304 Activities)
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Klebsiella pneumoniae (43867 Activities)
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Providencia rettgeri (925 Activities)
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Enterobacter cloacae (7976 Activities)
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Pseudomonas aeruginosa (123386 Activities)
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Staphylococcus aureus (210822 Activities)
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Enterococcus faecalis (29875 Activities)
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Streptococcus pneumoniae (31063 Activities)
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Streptococcus pyogenes (16140 Activities)
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Acinetobacter calcoaceticus (618 Activities)
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Providencia stuartii (425 Activities)
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Shigella (221 Activities)
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Staphylococcus epidermidis (22802 Activities)
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Serratia marcescens (3237 Activities)
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Moraxella bovis (17 Activities)
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Mus musculus (284745 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: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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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: 378.38 | Molecular Weight (Monoisotopic): 378.1503 | AlogP: 1.65 | #Rotatable Bonds: 3 |
| Polar Surface Area: 91.80 | Molecular Species: ACID | HBA: 6 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 5.38 | CX Basic pKa: 6.05 | CX LogP: 1.09 | CX LogD: 0.06 |
| Aromatic Rings: 2 | Heavy Atoms: 27 | QED Weighted: 0.79 | Np Likeness Score: -0.51 |
References
| 1. Miyamoto T, Matsumoto J, Chiba K, Egawa H, Shibamori K, Minamida A, Nishimura Y, Okada H, Kataoka M, Fujita M.. (1990) Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency., 33 (6): [PMID:2342057] [10.1021/jm00168a018] |
| 2. Domagala JM, Hagen SE, Heifetz CL, Hutt MP, Mich TF, Sanchez JP, Trehan AK.. (1988) 7-substituted 5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3- quinolinecarboxylic acids: synthesis and biological activity of a new class of quinolone antibacterials., 31 (3): [PMID:3346869] [10.1021/jm00398a003] |
| 3. Cecchetti V, Clementi S, Cruciani G, Fravolini A, Pagella PG, Savino A, Tabarrini O.. (1995) 6-Aminoquinolones: a new class of quinolone antibacterials?, 38 (6): [PMID:7699714] [10.1021/jm00006a017] |
Source
Source(1):