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ID: ALA608117
Max Phase: Preclinical
Molecular Formula: C17H16O6
Molecular Weight: 316.31
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1ccc2c(c1)C(=O)C1=C(C[C@H](CC(=O)O)O[C@@H]1C)C2=O
Standard InChI: InChI=1S/C17H16O6/c1-8-15-13(6-10(23-8)7-14(18)19)16(20)11-4-3-9(22-2)5-12(11)17(15)21/h3-5,8,10H,6-7H2,1-2H3,(H,18,19)/t8-,10-/m1/s1
Standard InChI Key: YOYHYPFUGDLGQZ-PSASIEDQSA-N
Associated Targets(Human)
TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)
MDA-MB-231 (73002 Activities)
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Associated Targets(non-human)
Type-2 restriction enzyme XhoI (19 Activities)
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Saccharomyces cerevisiae (19171 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: 316.31 | Molecular Weight (Monoisotopic): 316.0947 | AlogP: 2.02 | #Rotatable Bonds: 3 |
| Polar Surface Area: 89.90 | Molecular Species: ACID | HBA: 5 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 3.57 | CX Basic pKa: | CX LogP: 1.21 | CX LogD: -2.14 |
| Aromatic Rings: 1 | Heavy Atoms: 23 | QED Weighted: 0.92 | Np Likeness Score: 1.19 |
References
| 1. Sperry J, Lorenzo-Castrillejo I, Brimble MA, Machín F.. (2009) Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum., 17 (20): [PMID:19783445] [10.1016/j.bmc.2009.08.064] |
| 2. Heapy AM, Patterson AV, Smaill JB, Jamieson SM, Guise CP, Sperry J, Hume PA, Rathwell K, Brimble MA.. (2013) Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions., 21 (24): [PMID:24436995] [10.1016/j.bmc.2013.09.052] |
Source
Source(1):