ID: ALA88808
Chembl Id: CHEMBL88808
PubChem CID: 10970861
Max Phase: Preclinical
Molecular Formula: C19H24NO5P
Molecular Weight: 377.38
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: NC(CCc1ccccc1)P(=O)(O)CC(Cc1ccc(O)cc1)C(=O)O
Standard InChI: InChI=1S/C19H24NO5P/c20-18(11-8-14-4-2-1-3-5-14)26(24,25)13-16(19(22)23)12-15-6-9-17(21)10-7-15/h1-7,9-10,16,18,21H,8,11-13,20H2,(H,22,23)(H,24,25)
Standard InChI Key: STVSJGZHUJJREA-UHFFFAOYSA-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: 377.38 | Molecular Weight (Monoisotopic): 377.1392 | AlogP: 2.82 | #Rotatable Bonds: 9 |
| Polar Surface Area: 120.85 | Molecular Species: ZWITTERION | HBA: 4 | HBD: 4 |
| #RO5 Violations: ┄ | HBA (Lipinski): 6 | HBD (Lipinski): 5 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: -0.06 | CX Basic pKa: 10.06 | CX LogP: 1.46 | CX LogD: -1.42 |
| Aromatic Rings: 2 | Heavy Atoms: 26 | QED Weighted: 0.50 | Np Likeness Score: 0.44 |
| 1. Grembecka J, Mucha A, Cierpicki T, Kafarski P.. (2003) The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity., 46 (13): [PMID:12801228] [10.1021/jm030795v] |
| 2. Vassiliou S, Węglarz-Tomczak E, Berlicki Ł, Pawełczak M, Nocek B, Mulligan R, Joachimiak A, Mucha A.. (2014) Structure-guided, single-point modifications in the phosphinic dipeptide structure yield highly potent and selective inhibitors of neutral aminopeptidases., 57 (19): [PMID:25192493] [10.1021/jm501071f] |
| 3. Węglarz-Tomczak E, Vassiliou S, Mucha A.. (2016) Discovery of potent and selective inhibitors of human aminopeptidases ERAP1 and ERAP2 by screening libraries of phosphorus-containing amino acid and dipeptide analogues., 26 (16): [PMID:27390066] [10.1016/j.bmcl.2016.06.062] |
| 4. Amin SA, Adhikari N, Jha T.. (2018) Design of Aminopeptidase N Inhibitors as Anti-cancer Agents., 61 (15): [PMID:29630364] [10.1021/acs.jmedchem.7b00782] |
| 5. Talma M, Maślanka M, Mucha A.. (2019) Recent developments in the synthesis and applications of phosphinic peptide analogs., 29 (9): [PMID:30846252] [10.1016/j.bmcl.2019.02.034] |
| 6. Mills B, Isaac RE, Foster R.. (2021) Metalloaminopeptidases of the Protozoan Parasite Plasmodium falciparum as Targets for the Discovery of Novel Antimalarial Drugs., 64 (4.0): [PMID:33534577] [10.1021/acs.jmedchem.0c01721] |
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