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ID: ALA2348814
Max Phase: Preclinical
Molecular Formula: C22H19N3O4
Molecular Weight: 389.41
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1ccc(OC(C)C(=O)Nc2ccc3oc(-c4ccncc4)nc3c2)cc1
Standard InChI: InChI=1S/C22H19N3O4/c1-14(28-18-6-4-17(27-2)5-7-18)21(26)24-16-3-8-20-19(13-16)25-22(29-20)15-9-11-23-12-10-15/h3-14H,1-2H3,(H,24,26)
Standard InChI Key: IVGPIXAITZGSKF-UHFFFAOYSA-N
Associated Targets(Human)
HEK293 (82097 Activities)
HeLa (62764 Activities)
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IMPDH2 Tclin Inosine-5'-monophosphate dehydrogenase 2 (1326 Activities)
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GMPR2 Tbio GMP reductase 2 (49 Activities)
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Associated Targets(non-human)
Toxoplasma gondii (4585 Activities)
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CHO (4503 Activities)
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Inosine-5'-monophosphate dehydrogenase, probable (496 Activities)
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Mycobacterium tuberculosis (203094 Activities)
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guaB Inosine-5'-monophosphate dehydrogenase (11 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: 389.41 | Molecular Weight (Monoisotopic): 389.1376 | AlogP: 4.30 | #Rotatable Bonds: 6 |
| Polar Surface Area: 86.48 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 12.38 | CX Basic pKa: 2.83 | CX LogP: 3.29 | CX LogD: 3.29 |
| Aromatic Rings: 4 | Heavy Atoms: 29 | QED Weighted: 0.53 | Np Likeness Score: -1.63 |
References
| 1. Gorla SK, Kavitha M, Zhang M, Chin JE, Liu X, Striepen B, Makowska-Grzyska M, Kim Y, Joachimiak A, Hedstrom L, Cuny GD.. (2013) Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5'-monophosphate dehydrogenase., 56 (10): [PMID:23668331] [10.1021/jm400241j] |
| 2. Chacko S, Boshoff HIM, Singh V, Ferraris DM, Gollapalli DR, Zhang M, Lawson AP, Pepi MJ, Joachimiak A, Rizzi M, Mizrahi V, Cuny GD, Hedstrom L.. (2018) Expanding Benzoxazole-Based Inosine 5'-Monophosphate Dehydrogenase (IMPDH) Inhibitor Structure-Activity As Potential Antituberculosis Agents., 61 (11): [PMID:29746130] [10.1021/acs.jmedchem.7b01839] |
Source
Source(1):