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ID: ALA2348796
Max Phase: Preclinical
Molecular Formula: C21H15Cl2N3O3
Molecular Weight: 428.28
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: C[C@H](Oc1cccc(Cl)c1Cl)C(=O)Nc1ccc2oc(-c3ccncc3)nc2c1
Standard InChI: InChI=1S/C21H15Cl2N3O3/c1-12(28-18-4-2-3-15(22)19(18)23)20(27)25-14-5-6-17-16(11-14)26-21(29-17)13-7-9-24-10-8-13/h2-12H,1H3,(H,25,27)/t12-/m0/s1
Standard InChI Key: HRXGXBGJVNUGSX-LBPRGKRZSA-N
Associated Targets(Human)
IMPDH2 Tclin Inosine-5'-monophosphate dehydrogenase 2 (1326 Activities)
GMPR2 Tbio GMP reductase 2 (49 Activities)
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Associated Targets(non-human)
Toxoplasma gondii (4585 Activities)
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Liver (8163 Activities)
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Inosine-5'-monophosphate dehydrogenase, probable (496 Activities)
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guaB Inosine-5'-monophosphate dehydrogenase (29 Activities)
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Mycobacterium tuberculosis (203094 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: 428.28 | Molecular Weight (Monoisotopic): 427.0490 | AlogP: 5.60 | #Rotatable Bonds: 5 |
| Polar Surface Area: 77.25 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 1 |
| #RO5 Violations: 1 | HBA (Lipinski): 6 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 12.38 | CX Basic pKa: 2.83 | CX LogP: 4.66 | CX LogD: 4.66 |
| Aromatic Rings: 4 | Heavy Atoms: 29 | QED Weighted: 0.45 | Np Likeness Score: -1.90 |
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. Mandapati K, Gorla SK, House AL, McKenney ES, Zhang M, Rao SN, Gollapalli DR, Mann BJ, Goldberg JB, Cuny GD, Glomski IJ, Hedstrom L.. (2014) Repurposing cryptosporidium inosine 5'-monophosphate dehydrogenase inhibitors as potential antibacterial agents., 5 (8): [PMID:25147601] [10.1021/ml500203p] |
| 3. 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] |
| 4. Juvale K, Shaik A, Kirubakaran S.. (2019) Inhibitors of inosine 5'-monophosphate dehydrogenase as emerging new generation antimicrobial agents., 10 (8): [PMID:31534651] [10.1039/C9MD00179D] |
Source
Source(1):