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ID: ALA424704
Max Phase: Preclinical
Molecular Formula: C26H24N2O4
Molecular Weight: 428.49
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): 1-[2-(Trityloxy)Ethoxymethyl]Uracil
Synonyms from Alternative Forms(1):
Canonical SMILES: O=c1ccn(COCCOC(c2ccccc2)(c2ccccc2)c2ccccc2)c(=O)[nH]1
Standard InChI: InChI=1S/C26H24N2O4/c29-24-16-17-28(25(30)27-24)20-31-18-19-32-26(21-10-4-1-5-11-21,22-12-6-2-7-13-22)23-14-8-3-9-15-23/h1-17H,18-20H2,(H,27,29,30)
Standard InChI Key: QEKAGWDUKXATPZ-UHFFFAOYSA-N
Associated Targets(Human)
Liver microsomes 16955 Activities
dUTP pyrophosphatase 446 Activities
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Associated Targets(non-human)
L6 7924 Activities
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dUTP pyrophosphatase 205 Activities
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Plasmodium falciparum 966862 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: 428.49 | Molecular Weight (Monoisotopic): 428.1736 | AlogP: 3.52 | #Rotatable Bonds: 9 |
| Polar Surface Area: 73.32 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.71 | CX Basic pKa: | CX LogP: 4.54 | CX LogD: 4.54 |
| Aromatic Rings: 4 | Heavy Atoms: 32 | QED Weighted: 0.33 | Np Likeness Score: -0.39 |
References
| 1. Nguyen C, Ruda GF, Schipani A, Kasinathan G, Leal I, Musso-Buendia A, Kaiser M, Brun R, Ruiz-Pérez LM, Sahlberg BL, Johansson NG, Gonzalez-Pacanowska D, Gilbert IH.. (2006) Acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase., 49 (14): [PMID:16821778] [10.1021/jm060126s] |
| 2. Recio E, Musso-Buendía A, Vidal AE, Ruda GF, Kasinathan G, Nguyen C, Ruiz-Pérez LM, Gilbert IH, González-Pacanowska D.. (2011) Site-directed mutagenesis provides insights into the selective binding of trityl derivatives to Plasmodium falciparum dUTPase., 46 (8): [PMID:21600680] [10.1016/j.ejmech.2011.04.052] |
| 3. Miyahara S, Miyakoshi H, Yokogawa T, Chong KT, Taguchi J, Muto T, Endoh K, Yano W, Wakasa T, Ueno H, Takao Y, Fujioka A, Hashimoto A, Itou K, Yamamura K, Nomura M, Nagasawa H, Shuto S, Fukuoka M.. (2012) Discovery of a novel class of potent human deoxyuridine triphosphatase inhibitors remarkably enhancing the antitumor activity of thymidylate synthase inhibitors., 55 (7): [PMID:22339362] [10.1021/jm201628y] |
| 4. (2013) Uracil compound or salt thereof having human deoxyuridine triphosphatase inhibitory activity, |
Source
Source(2):