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ID: ALA3330910
Max Phase: Preclinical
Molecular Formula: C29H31ClN4O2
Molecular Weight: 503.05
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc(NC(C)CCCNC(=O)NC(c2ccccc2)c2ccc(Cl)cc2)c2ncccc2c1
Standard InChI: InChI=1S/C29H31ClN4O2/c1-20(33-26-19-25(36-2)18-23-11-7-16-31-28(23)26)8-6-17-32-29(35)34-27(21-9-4-3-5-10-21)22-12-14-24(30)15-13-22/h3-5,7,9-16,18-20,27,33H,6,8,17H2,1-2H3,(H2,32,34,35)
Standard InChI Key: LKYQNUHVCKULNM-UHFFFAOYSA-N
Associated Targets(Human)
CCRF-CEM (65223 Activities)
HeLa (62764 Activities)
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SW-620 (52400 Activities)
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MCF7 (126967 Activities)
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Associated Targets(non-human)
L1210 (27553 Activities)
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Lipoxygenase (149 Activities)
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Plasmodium falciparum (966862 Activities)
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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: 503.05 | Molecular Weight (Monoisotopic): 502.2136 | AlogP: 6.57 | #Rotatable Bonds: 10 |
| Polar Surface Area: 75.28 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 3 |
| #RO5 Violations: 2 | HBA (Lipinski): 6 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: | CX Basic pKa: 4.08 | CX LogP: 5.46 | CX LogD: 5.46 |
| Aromatic Rings: 4 | Heavy Atoms: 36 | QED Weighted: 0.21 | Np Likeness Score: -1.13 |
References
| 1. Pavić K, Perković I, Cindrić M, Pranjić M, Martin-Kleiner I, Kralj M, Schols D, Hadjipavlou-Litina D, Katsori AM, Zorc B.. (2014) Novel semicarbazides and ureas of primaquine with bulky aryl or hydroxyalkyl substituents: synthesis, cytostatic and antioxidative activity., 86 [PMID:25203780] [10.1016/j.ejmech.2014.09.013] |
| 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):