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ID: ALA101135
Max Phase: Preclinical
Molecular Formula: C28H26N2O3
Molecular Weight: 438.53
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Cc1cn(C/C=C\COC(c2ccccc2)(c2ccccc2)c2ccccc2)c(=O)[nH]c1=O
Standard InChI: InChI=1S/C28H26N2O3/c1-22-21-30(27(32)29-26(22)31)19-11-12-20-33-28(23-13-5-2-6-14-23,24-15-7-3-8-16-24)25-17-9-4-10-18-25/h2-18,21H,19-20H2,1H3,(H,29,31,32)/b12-11-
Standard InChI Key: BHMZJUVAVWRNLN-QXMHVHEDSA-N
Associated Targets(Human)
Thymidine kinase, cytosolic 627 Activities
Thymidine kinase, mitochondrial 96 Activities
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Associated Targets(non-human)
Thymidine kinase 140 Activities
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Deoxynucleoside kinase 95 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: 438.53 | Molecular Weight (Monoisotopic): 438.1943 | AlogP: 4.41 | #Rotatable Bonds: 8 |
| Polar Surface Area: 64.09 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 10.31 | CX Basic pKa: | CX LogP: 5.40 | CX LogD: 5.40 |
| Aromatic Rings: 4 | Heavy Atoms: 33 | QED Weighted: 0.33 | Np Likeness Score: -0.25 |
References
| 1. Hernández AI, Balzarini J, Rodríguez-Barrios F, San-Félix A, Karlsson A, Gago F, Camarasa MJ, Pérez-Pérez MJ.. (2003) Improving the selectivity of acyclic nucleoside analogues as inhibitors of human mitochondrial thymidine kinase: replacement of a triphenylmethoxy moiety with substituted amines and carboxamides., 13 (18): [PMID:12941326] [10.1016/s0960-894x(03)00639-5] |
| 2. Hernández AI, Balzarini J, Karlsson A, Camarasa MJ, Pérez-Pérez MJ.. (2002) Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase., 45 (19): [PMID:12213066] [10.1021/jm011128+] |
| 3. Hernandez AI, Familiar O, Negri A, Rodríguez-Barrios F, Gago F, Karlsson A, Camarasa MJ, Balzarini J, Pérez-Pérez MJ.. (2006) N1-substituted thymine derivatives as mitochondrial thymidine kinase (TK-2) inhibitors., 49 (26): [PMID:17181158] [10.1021/jm0610550] |
| 4. Van Poecke S, Negri A, Gago F, Van Daele I, Solaroli N, Karlsson A, Balzarini J, Van Calenbergh S.. (2010) 3'-[4-Aryl-(1,2,3-triazol-1-yl)]-3'-deoxythymidine analogues as potent and selective inhibitors of human mitochondrial thymidine kinase., 53 (7): [PMID:20218622] [10.1021/jm901532h] |
Source
Source(1):