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ID: ALA3955519
Max Phase: Preclinical
Molecular Formula: C21H26ClN5O4
Molecular Weight: 447.92
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCOC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NC(C4CC4)C4CC4)nc(Cl)nc31)[C@H](O)[C@@H]2O
Standard InChI: InChI=1S/C21H26ClN5O4/c1-2-31-19(30)21-7-11(21)14(15(28)16(21)29)27-8-23-13-17(25-20(22)26-18(13)27)24-12(9-3-4-9)10-5-6-10/h8-12,14-16,28-29H,2-7H2,1H3,(H,24,25,26)/t11-,14-,15+,16+,21+/m1/s1
Standard InChI Key: IRHYVDDJDDMRKD-QNEDUEMWSA-N
Associated Targets(Human)
Serotonin 1a (5-HT1a) receptor 14969 Activities
Serotonin 1b (5-HT1b) receptor 2801 Activities
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Translocator protein 484 Activities
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Serotonin 1d (5-HT1d) receptor 2897 Activities
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Serotonin 1e (5-HT1e) receptor 696 Activities
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Serotonin 4 (5-HT4) receptor 2068 Activities
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Serotonin 6 (5-HT6) receptor 9749 Activities
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Serotonin 7 (5-HT7) receptor 5576 Activities
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Serotonin 3a (5-HT3a) receptor 3366 Activities
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Serotonin 2a (5-HT2a) receptor 14758 Activities
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Serotonin 2b (5-HT2b) receptor 10323 Activities
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Serotonin 2c (5-HT2c) receptor 11471 Activities
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Adenosine A1 receptor 17603 Activities
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Adenosine A2a receptor 16305 Activities
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Transmembrane domain-containing protein TMIGD3 200 Activities
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Serotonin 5a (5-HT5a) receptor 1433 Activities
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Adenosine A3 receptor 15931 Activities
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Associated Targets(non-human)
Adenosine A3 receptor 257 Activities
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Enterovirus A71 1246 Activities
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Vero 76 245 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: 447.92 | Molecular Weight (Monoisotopic): 447.1673 | AlogP: 1.93 | #Rotatable Bonds: 7 |
| Polar Surface Area: 122.39 | Molecular Species: NEUTRAL | HBA: 9 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 9 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 13.12 | CX Basic pKa: 2.17 | CX LogP: 1.62 | CX LogD: 1.62 |
| Aromatic Rings: 2 | Heavy Atoms: 31 | QED Weighted: 0.43 | Np Likeness Score: 0.12 |
References
| 1. Tosh DK, Ciancetta A, Warnick E, Crane S, Gao ZG, Jacobson KA.. (2016) Structure-Based Scaffold Repurposing for G Protein-Coupled Receptors: Transformation of Adenosine Derivatives into 5HT2B/5HT2C Serotonin Receptor Antagonists., 59 (24): [PMID:27933810] [10.1021/acs.jmedchem.6b01183] |
| 2. Tosh DK, Rao H, Bitant A, Salmaso V, Mannes P, Lieberman DI, Vaughan KL, Mattison JA, Rothwell AC, Auchampach JA, Ciancetta A, Liu N, Cui Z, Gao ZG, Reitman ML, Gavrilova O, Jacobson KA.. (2019) Design and in Vivo Characterization of A1 Adenosine Receptor Agonists in the Native Ribose and Conformationally Constrained (N)-Methanocarba Series., 62 (3): [PMID:30605331] [10.1021/acs.jmedchem.8b01662] |
| 3. Tosh DK,Toti KS,Hurst BL,Julander JG,Jacobson KA. (2020) Structure activity relationship of novel antiviral nucleosides against Enterovirus A71., 30 (23): [PMID:33031923] [10.1016/j.bmcl.2020.127599] |
Source
Source(1):