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ID: ALA346196
Max Phase: Preclinical
Molecular Formula: C20H18N2O5
Molecular Weight: 366.37
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1
Standard InChI: InChI=1S/C20H18N2O5/c1-12-17(19(25)20(21)26)18-14(8-5-9-15(18)27-11-16(23)24)22(12)10-13-6-3-2-4-7-13/h2-9H,10-11H2,1H3,(H2,21,26)(H,23,24)
Standard InChI Key: FBGWHCFPQBQYNU-UHFFFAOYSA-N
Associated Targets(Human)
PLA2G2A Tchem Phospholipase A2 group IIA (1079 Activities)
PLA2G1B Tchem Phospholipase A2 group 1B (720 Activities)
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PLA2G2E Tchem Group IIE secretory phospholipase A2 (20 Activities)
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PLA2G5 Tchem Phospholipase A2 group V (238 Activities)
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PLA2G10 Tchem Group X secretory phospholipase A2 (219 Activities)
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Associated Targets(non-human)
PLA2G1B Phospholipase A2 group 1B (227 Activities)
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Cavia porcellus (23802 Activities)
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Pla2g1b Phospholipase A2 group 1B (51 Activities)
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Pla2g2a Phospholipase A2, membrane associated (39 Activities)
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Pla2g2e Group IIE secretory phospholipase A2 (19 Activities)
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Pla2g5 Phospholipase A2 group V (31 Activities)
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Pla2g10 Group X secretory phospholipase A2 (43 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: 366.37 | Molecular Weight (Monoisotopic): 366.1216 | AlogP: 2.13 | #Rotatable Bonds: 7 |
| Polar Surface Area: 111.62 | Molecular Species: ACID | HBA: 5 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 3.56 | CX Basic pKa: | CX LogP: 2.25 | CX LogD: -1.11 |
| Aromatic Rings: 3 | Heavy Atoms: 27 | QED Weighted: 0.49 | Np Likeness Score: -0.78 |
References
| 1. Draheim SE, Bach NJ, Dillard RD, Berry DR, Carlson DG, Chirgadze NY, Clawson DK, Hartley LW, Johnson LM, Jones ND, McKinney ER, Mihelich ED, Olkowski JL, Schevitz RW, Smith AC, Snyder DW, Sommers CD, Wery JP.. (1996) Indole inhibitors of human nonpancreatic secretory phospholipase A2. 3. Indole-3-glyoxamides., 39 (26): [PMID:8978844] [10.1021/jm960487f] |
| 2. Smart BP, Oslund RC, Walsh LA, Gelb MH.. (2006) The first potent inhibitor of mammalian group X secreted phospholipase A2: elucidation of sites for enhanced binding., 49 (10): [PMID:16686528] [10.1021/jm060136t] |
| 3. Robello M, Barresi E, Baglini E, Salerno S, Taliani S, Settimo FD.. (2021) The Alpha Keto Amide Moiety as a Privileged Motif in Medicinal Chemistry: Current Insights and Emerging Opportunities., 64 (7.0): [PMID:33764065] [10.1021/acs.jmedchem.0c01808] |
Source
Source(1):