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ID: ALA222252
Max Phase: Preclinical
Molecular Formula: C21H24N4
Molecular Weight: 332.45
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCN(CC)CCNc1c2ccccc2nc2c1[nH]c1ccccc12
Standard InChI: InChI=1S/C21H24N4/c1-3-25(4-2)14-13-22-19-15-9-5-7-11-17(15)23-20-16-10-6-8-12-18(16)24-21(19)20/h5-12,24H,3-4,13-14H2,1-2H3,(H,22,23)
Standard InChI Key: BWWJYRDFOAYKCH-UHFFFAOYSA-N
Associated Targets(Human)
HepG2 196354 Activities
CA46 271 Activities
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Ramos 1218 Activities
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Raji 5516 Activities
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HCT-116 91556 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: 332.45 | Molecular Weight (Monoisotopic): 332.2001 | AlogP: 4.62 | #Rotatable Bonds: 6 |
| Polar Surface Area: 43.95 | Molecular Species: BASE | HBA: 3 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 13.78 | CX Basic pKa: 9.43 | CX LogP: 3.84 | CX LogD: 1.37 |
| Aromatic Rings: 4 | Heavy Atoms: 25 | QED Weighted: 0.54 | Np Likeness Score: -0.88 |
References
| 1. Ou TM, Lu YJ, Zhang C, Huang ZS, Wang XD, Tan JH, Chen Y, Ma DL, Wong KY, Tang JC, Chan AS, Gu LQ.. (2007) Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc by quindoline derivatives., 50 (7): [PMID:17346034] [10.1021/jm0610088] |
| 2. Boddupally PV, Hahn S, Beman C, De B, Brooks TA, Gokhale V, Hurley LH.. (2012) Anticancer activity and cellular repression of c-MYC by the G-quadruplex-stabilizing 11-piperazinylquindoline is not dependent on direct targeting of the G-quadruplex in the c-MYC promoter., 55 (13): [PMID:22691117] [10.1021/jm300282c] |
| 3. Mendes E, Bahls B, Aljnadi IM, Paulo A.. (2022) Indoloquinolines as scaffolds for the design of potent G-quadruplex ligands., 72 [PMID:35716866] [10.1016/j.bmcl.2022.128862] |
| 4. Nuthakki VK, Mudududdla R, Bharate SB.. (2022) Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids., 227 [PMID:34710743] [10.1016/j.ejmech.2021.113938] |
Source
Source(1):