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ID: ALA345998
Max Phase: Preclinical
Molecular Formula: C22H18N2O6
Molecular Weight: 406.39
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCC1(O)CC(=O)OCc2c1cc1n(c2=O)Cc2cc3cc4c(cc3nc2-1)OCO4
Standard InChI: InChI=1S/C22H18N2O6/c1-2-22(27)7-19(25)28-9-13-14(22)5-16-20-12(8-24(16)21(13)26)3-11-4-17-18(30-10-29-17)6-15(11)23-20/h3-6,27H,2,7-10H2,1H3
Standard InChI Key: MWDHYRWFFNTLOV-UHFFFAOYSA-N
Associated Targets(Human)
DNA topoisomerase I 7553 Activities
A-427 643 Activities
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PC-3 62116 Activities
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K562 73714 Activities
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MCF7 126967 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: 406.39 | Molecular Weight (Monoisotopic): 406.1165 | AlogP: 2.20 | #Rotatable Bonds: 1 |
| Polar Surface Area: 99.88 | Molecular Species: NEUTRAL | HBA: 8 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 8 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 13.81 | CX Basic pKa: 3.44 | CX LogP: 0.78 | CX LogD: 0.78 |
| Aromatic Rings: 3 | Heavy Atoms: 30 | QED Weighted: 0.48 | Np Likeness Score: 0.88 |
References
| 1. Lavergne O, Lesueur-Ginot L, Pla Rodas F, Kasprzyk PG, Pommier J, Demarquay D, Prévost G, Ulibarri G, Rolland A, Schiano-Liberatore AM, Harnett J, Pons D, Camara J, Bigg DC.. (1998) Homocamptothecins: synthesis and antitumor activity of novel E-ring-modified camptothecin analogues., 41 (27): [PMID:9876111] [10.1021/jm980400l] |
| 2. Huang Q, Wang L, Lu W.. (2013) Evolution in medicinal chemistry of E-ring-modified Camptothecin analogs as anticancer agents., 63 [PMID:23578545] [10.1016/j.ejmech.2013.01.058] |
Source
Source(1):