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ID: ALA204593
Max Phase: Preclinical
Molecular Formula: C14H19FN2O5S
Molecular Weight: 346.38
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Cc1cc(S(=O)(=O)N[C@@H](C(=O)NO)C2CCOCC2)ccc1F
Standard InChI: InChI=1S/C14H19FN2O5S/c1-9-8-11(2-3-12(9)15)23(20,21)17-13(14(18)16-19)10-4-6-22-7-5-10/h2-3,8,10,13,17,19H,4-7H2,1H3,(H,16,18)/t13-/m1/s1
Standard InChI Key: LUCFRFDOOYLALP-CYBMUJFWSA-N
Associated Targets(Human)
ACE Tclin Angiotensin-converting enzyme (1423 Activities)
ECE1 Tchem Endothelin-converting enzyme 1 (674 Activities)
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MME Tclin Neprilysin (838 Activities)
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ADAM17 Tchem ADAM17 (3550 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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MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)
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MMP9 Tchem Matrix metalloproteinase 9 (6779 Activities)
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MMP14 Tchem Matrix metalloproteinase 14 (1592 Activities)
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Associated Targets(non-human)
lef Anthrax lethal factor (7585 Activities)
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Mus musculus (284745 Activities)
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Rattus norvegicus (775804 Activities)
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Cavia porcellus (23802 Activities)
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Oryctolagus cuniculus (11301 Activities)
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Canis familiaris (36305 Activities)
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Rhesus monkey (3147 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: 346.38 | Molecular Weight (Monoisotopic): 346.0999 | AlogP: 0.71 | #Rotatable Bonds: 5 |
| Polar Surface Area: 104.73 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.68 | CX Basic pKa: | CX LogP: 0.76 | CX LogD: 0.74 |
| Aromatic Rings: 1 | Heavy Atoms: 23 | QED Weighted: 0.54 | Np Likeness Score: -1.46 |
References
| 1. Xiong Y, Wiltsie J, Woods A, Guo J, Pivnichny JV, Tang W, Bansal A, Cummings RT, Cunningham BR, Friedlander AM, Douglas CM, Salowe SP, Zaller DM, Scolnick EM, Schmatz DM, Bartizal K, Hermes JD, MacCoss M, Chapman KT.. (2006) The discovery of a potent and selective lethal factor inhibitor for adjunct therapy of anthrax infection., 16 (4): [PMID:16338135] [10.1016/j.bmcl.2005.10.088] |
| 2. Williams JD, Khan AR, Cardinale SC, Butler MM, Bowlin TL, Peet NP.. (2014) Small molecule inhibitors of anthrax lethal factor toxin., 22 (1): [PMID:24290062] [10.1016/j.bmc.2013.11.009] |
| 3. Hou R, He Y, Yan G, Hou S, Xie Z, Liao C.. (2021) Zinc enzymes in medicinal chemistry., 226 [PMID:34624823] [10.1016/j.ejmech.2021.113877] |
Source
Source(1):