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ID: ALA265096
Max Phase: Preclinical
Molecular Formula: C31H26N2O6
Molecular Weight: 522.56
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): MRS-1334
Synonyms from Alternative Forms(1):
Canonical SMILES: CCO/C(O)=C1\C(C)=NC(c2ccccc2)=C(C(=O)OCc2ccc([N+](=O)[O-])cc2)C1C#Cc1ccccc1
Standard InChI: InChI=1S/C31H26N2O6/c1-3-38-30(34)27-21(2)32-29(24-12-8-5-9-13-24)28(26(27)19-16-22-10-6-4-7-11-22)31(35)39-20-23-14-17-25(18-15-23)33(36)37/h4-15,17-18,26,34H,3,20H2,1-2H3/b30-27+
Standard InChI Key: MOUCZLGFFQYULK-KDJFERLWSA-N
Associated Targets(Human)
Adenosine A3 receptor 15931 Activities
Adenosine receptors; A1 & A3 1051 Activities
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Associated Targets(non-human)
Adenosine A1 receptor 6163 Activities
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Adenosine A2a receptor 3360 Activities
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Adenosine A3 receptor 846 Activities
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Adenosine receptor A2a and A3 172 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: 522.56 | Molecular Weight (Monoisotopic): 522.1791 | AlogP: 6.00 | #Rotatable Bonds: 7 |
| Polar Surface Area: 111.26 | Molecular Species: ACID | HBA: 7 | HBD: 1 |
| #RO5 Violations: 2 | HBA (Lipinski): 8 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: 5.40 | CX Basic pKa: 3.12 | CX LogP: 6.45 | CX LogD: 4.45 |
| Aromatic Rings: 3 | Heavy Atoms: 39 | QED Weighted: 0.13 | Np Likeness Score: -0.78 |
References
| 1. Jiang J, van Rhee AM, Chang L, Patchornik A, Ji XD, Evans P, Melman N, Jacobson KA.. (1997) Structure-activity relationships of 4-(phenylethynyl)-6-phenyl-1,4-dihydropyridines as highly selective A3 adenosine receptor antagonists., 40 (16): [PMID:9258367] [10.1021/jm970091j] |
| 2. Kim YC, de Zwart M, Chang L, Moro S, von Frijtag Drabbe Künzel JK, Melman N, IJzerman AP, Jacobson KA.. (1998) Derivatives of the triazoloquinazoline adenosine antagonist (CGS 15943) having high potency at the human A2B and A3 receptor subtypes., 41 (15): [PMID:9667972] [10.1021/jm980094b] |
| 3. Li AH, Moro S, Melman N, Ji XD, Jacobson KA.. (1998) Structure-activity relationships and molecular modeling of 3, 5-diacyl-2,4-dialkylpyridine derivatives as selective A3 adenosine receptor antagonists., 41 (17): [PMID:9703464] [10.1021/jm980093j] |
| 4. Baraldi PG, Preti D, Borea PA, Varani K.. (2012) Medicinal chemistry of A₃ adenosine receptor modulators: pharmacological activities and therapeutic implications., 55 (12): [PMID:22468757] [10.1021/jm300087j] |
Source
Source(1):