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ID: ALA1801026
Max Phase: Preclinical
Molecular Formula: C32H39NO7
Molecular Weight: 549.66
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCCCCCCCc1ccc(OCC(=O)Cn2cc(C(=O)CCCCC(=O)O)c3cc(C(=O)O)ccc32)cc1
Standard InChI: InChI=1S/C32H39NO7/c1-2-3-4-5-6-7-10-23-13-16-26(17-14-23)40-22-25(34)20-33-21-28(30(35)11-8-9-12-31(36)37)27-19-24(32(38)39)15-18-29(27)33/h13-19,21H,2-12,20,22H2,1H3,(H,36,37)(H,38,39)
Standard InChI Key: QLVBBRQNAYNNQR-UHFFFAOYSA-N
Associated Targets(Human)
PLA2G4A Tchem Cytosolic phospholipase A2 (785 Activities)
Associated Targets(non-human)
Liver microsomes (8692 Activities)
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Plasma (6361 Activities)
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Intestine (514 Activities)
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Pla2g6 85 kDa calcium-independent phospholipase A2 (4 Activities)
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PLA2G1B Phospholipase A2 group 1B (227 Activities)
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Por NADPH--cytochrome P450 reductase (42 Activities)
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Por NADPH--cytochrome P450 reductase (13 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: 549.66 | Molecular Weight (Monoisotopic): 549.2727 | AlogP: 6.72 | #Rotatable Bonds: 19 |
| Polar Surface Area: 122.90 | Molecular Species: ACID | HBA: 6 | HBD: 2 |
| #RO5 Violations: 2 | HBA (Lipinski): 8 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: 3.49 | CX Basic pKa: | CX LogP: 7.17 | CX LogD: 0.84 |
| Aromatic Rings: 3 | Heavy Atoms: 40 | QED Weighted: 0.13 | Np Likeness Score: -0.27 |
References
| 1. Bovens S, Schulze Elfringhoff A, Kaptur M, Reinhardt D, Schäfers M, Lehr M.. (2010) 1-(5-Carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A2α: effect of substituents in position 3 of the indole scaffold on inhibitory potency, metabolic stability, solubility, and bioavailability., 53 (23): [PMID:21067218] [10.1021/jm101094p] |
| 2. Arnsmann M, Hanekamp W, Elfringhoff AS, Lehr M.. (2017) Structure-activity relationship studies on 1-(2-oxopropyl)indole-5-carboxylic acids acting as inhibitors of cytosolic phospholipase A2α: Effect of substituents at the indole 3-position on activity, solubility, and metabolic stability., 125 [PMID:27810597] [10.1016/j.ejmech.2016.10.039] |
Source
Source(1):