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ID: ALA3884615
Max Phase: Preclinical
Molecular Formula: C23H27ClN6O3
Molecular Weight: 470.96
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc(NC(C)CCCNC(=O)NNC(=O)Nc2cccc(Cl)c2)c2ncccc2c1
Standard InChI: InChI=1S/C23H27ClN6O3/c1-15(27-20-14-19(33-2)12-16-7-5-10-25-21(16)20)6-4-11-26-22(31)29-30-23(32)28-18-9-3-8-17(24)13-18/h3,5,7-10,12-15,27H,4,6,11H2,1-2H3,(H2,26,29,31)(H2,28,30,32)
Standard InChI Key: FWBXNFZDDLJXPB-UHFFFAOYSA-N
Associated Targets(non-human)
Plasmodium falciparum (966862 Activities)
L6 (7924 Activities)
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Mycobacterium tuberculosis (203094 Activities)
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Mycobacterium avium complex sp. (178 Activities)
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Mycobacterium avium (4587 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: 470.96 | Molecular Weight (Monoisotopic): 470.1833 | AlogP: 4.51 | #Rotatable Bonds: 8 |
| Polar Surface Area: 116.41 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 5 |
| #RO5 Violations: 0 | HBA (Lipinski): 9 | HBD (Lipinski): 5 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.84 | CX Basic pKa: 4.07 | CX LogP: 3.05 | CX LogD: 3.05 |
| Aromatic Rings: 3 | Heavy Atoms: 33 | QED Weighted: 0.25 | Np Likeness Score: -1.51 |
References
| 1. Perković I, Antunović M, Marijanović I, Pavić K, Ester K, Kralj M, Vlainić J, Kosalec I, Schols D, Hadjipavlou-Litina D, Pontiki E, Zorc B.. (2016) Novel urea and bis-urea primaquine derivatives with hydroxyphenyl or halogenphenyl substituents: Synthesis and biological evaluation., 124 [PMID:27614409] [10.1016/j.ejmech.2016.08.021] |
| 2. Levatić J, Pavić K, Perković I, Uzelac L, Ester K, Kralj M, Kaiser M, Rottmann M, Supek F, Zorc B.. (2018) Machine learning prioritizes synthesis of primaquine ureidoamides with high antimalarial activity and attenuated cytotoxicity., 146 [PMID:29407988] [10.1016/j.ejmech.2018.01.062] |
| 3. Pavić K, Perković I, Pospíšilová Š, Machado M, Fontinha D, Prudêncio M, Jampilek J, Coffey A, Endersen L, Rimac H, Zorc B.. (2018) Primaquine hybrids as promising antimycobacterial and antimalarial agents., 143 [PMID:29220797] [10.1016/j.ejmech.2017.11.083] |
Source
Source(1):