| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ID: ALA278722
Max Phase: Preclinical
Molecular Formula: C21H18N2O4S
Molecular Weight: 394.45
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CC1(C)Oc2c(c3nc4ccccc4nc3c3ccccc23)CC1S(=O)(=O)O
Standard InChI: InChI=1S/C21H18N2O4S/c1-21(2)17(28(24,25)26)11-14-19-18(22-15-9-5-6-10-16(15)23-19)12-7-3-4-8-13(12)20(14)27-21/h3-10,17H,11H2,1-2H3,(H,24,25,26)
Standard InChI Key: HCHJSOSREULXTE-UHFFFAOYSA-N
Associated Targets(non-human)
Plasmodium falciparum 966862 Activities
Plasmodium berghei 192651 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
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 |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Properties
| Molecular Weight: 394.45 | Molecular Weight (Monoisotopic): 394.0987 | AlogP: 3.91 | #Rotatable Bonds: 1 |
| Polar Surface Area: 89.38 | Molecular Species: ACID | HBA: 5 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: -0.70 | CX Basic pKa: 1.23 | CX LogP: 2.00 | CX LogD: 1.48 |
| Aromatic Rings: 4 | Heavy Atoms: 28 | QED Weighted: 0.30 | Np Likeness Score: 0.48 |
References
| 1. de Andrade-Neto VF, Goulart MO, da Silva Filho JF, da Silva MJ, Pinto Mdo C, Pinto AV, Zalis MG, Carvalho LH, Krettli AU.. (2004) Antimalarial activity of phenazines from lapachol, beta-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo., 14 (5): [PMID:14980653] [10.1016/j.bmcl.2003.12.069] |
| 2. Prado-Prado FJ, García-Mera X, González-Díaz H.. (2010) Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species., 18 (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068] |
| 3. de Castro SL, Emery FS, da Silva Júnior EN.. (2013) Synthesis of quinoidal molecules: strategies towards bioactive compounds with an emphasis on lapachones., 69 [PMID:24095760] [10.1016/j.ejmech.2013.07.057] |
| 4. Gong Q, Hu J, Wang P, Li X, Zhang X.. (2021) A comprehensive review on β-lapachone: Mechanisms, structural modifications, and therapeutic potentials., 210 [PMID:33158575] [10.1016/j.ejmech.2020.112962] |
Source
Source(1):