ID: ALA3693855
PubChem CID: 135912154
Max Phase: Preclinical
Molecular Formula: C23H23N5O2
Molecular Weight: 401.47
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: Cc1ccc(-c2ccccc2Cc2nc3c(cnn3C3CCOCC3)c(=O)[nH]2)nc1
Standard InChI: InChI=1S/C23H23N5O2/c1-15-6-7-20(24-13-15)18-5-3-2-4-16(18)12-21-26-22-19(23(29)27-21)14-25-28(22)17-8-10-30-11-9-17/h2-7,13-14,17H,8-12H2,1H3,(H,26,27,29)
Standard InChI Key: JWGNAANHWCHYLX-UHFFFAOYSA-N
Molfile:
RDKit 2D
30 34 0 0 0 0 0 0 0 0999 V2000
8.8418 -0.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.7996 -1.5257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.5043 -0.7692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.2015 -1.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1938 -3.0126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4892 -3.7691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.7920 -3.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8915 -3.7585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8864 -5.2585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5847 -6.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2883 -5.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2935 -3.7495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5951 -3.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5973 -1.5031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2990 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.0000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4133 1.7530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.8032 3.1233 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.3115 2.9665 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6928 4.0817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3384 5.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.4233 6.5700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8628 6.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.2175 4.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1327 3.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2990 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.3383 -1.3500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.0000 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
2 3 2 0
3 4 1 0
4 5 2 0
5 6 1 0
6 7 2 0
7 2 1 0
5 8 1 0
8 9 2 0
9 10 1 0
10 11 2 0
11 12 1 0
12 13 2 0
13 8 1 0
13 14 1 0
14 15 1 0
15 16 2 0
16 17 1 0
17 18 2 0
18 19 1 0
19 20 2 0
20 21 1 0
21 17 1 0
21 22 1 0
22 23 1 0
23 24 1 0
24 25 1 0
25 26 1 0
26 27 1 0
27 22 1 0
18 28 1 0
28 29 2 0
28 30 1 0
30 15 1 0
M END| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| 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 |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
| Molecular Weight: 401.47 | Molecular Weight (Monoisotopic): 401.1852 | AlogP: 3.43 | #Rotatable Bonds: 4 |
| Polar Surface Area: 85.69 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 1 |
| #RO5 Violations: ┄ | HBA (Lipinski): 7 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: 9.16 | CX Basic pKa: 4.50 | CX LogP: 2.41 | CX LogD: 2.41 |
| Aromatic Rings: 4 | Heavy Atoms: 30 | QED Weighted: 0.57 | Np Likeness Score: -1.40 |
| 1. (2014) Compounds for the treatment of CNS disorders, |
| 2. Fisher, D A DA, Smith, J F JF, Pillar, J S JS, St Denis, S H SH and Cheng, J B JB. 1998-06-19 Isolation and characterization of PDE9A, a novel human cGMP-specific phosphodiesterase. [PMID:9624146] |
| 3. Boyle, Craig D CD and 20 more authors. 2005-05-02 Optimization of purine based PDE1/PDE5 inhibitors to a potent and selective PDE5 inhibitor for the treatment of male ED. [PMID:15837326] |
| 4. Wang, Huanchen H and 5 more authors. 2010-02-25 Insight into binding of phosphodiesterase-9A selective inhibitors by crystal structures and mutagenesis. [PMID:20121115] |
| 5. Verhoest, Patrick R PR and 15 more authors. 2012-11-08 Design and discovery of 6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (PF-04447943), a selective brain penetrant PDE9A inhibitor for the treatment of cognitive disorders. [PMID:22780914] |
| 6. Meng, Fei and 12 more authors. 2012-10-11 Structure-based discovery of highly selective phosphodiesterase-9A inhibitors and implications for inhibitor design. [PMID:22985069] |
| 7. Claffey, Michelle M MM and 23 more authors. 2012-11-08 Application of structure-based drug design and parallel chemistry to identify selective, brain penetrant, in vivo active phosphodiesterase 9A inhibitors. [PMID:23025719] |
| 8. Fiorito, Jole J and 10 more authors. 2013-02 Synthesis of quinoline derivatives: discovery of a potent and selective phosphodiesterase 5 inhibitor for the treatment of Alzheimer's disease. [PMID:23313637] |
| 9. Shao, Yong-xian YX and 11 more authors. 2014-12-26 Discovery of a phosphodiesterase 9A inhibitor as a potential hypoglycemic agent. [PMID:25432025] |
| 10. Cheng, Zhong-Bin ZB and 8 more authors. 2014-12-26 (±)-Torreyunlignans A-D, rare 8-9' linked neolignan enantiomers as phosphodiesterase-9A inhibitors from Torreya yunnanensis. [PMID:25495612] |
| 11. Guo, Yan-Qiong YQ and 6 more authors. 2018-01-20 Prenylated flavonoids as potent phosphodiesterase-4 inhibitors from Morus alba: Isolation, modification, and structure-activity relationship study. [PMID:29291443] |
| 12. Wu, Yinuo Y and 13 more authors. 2019-04-25 Discovery of Potent, Selective, and Orally Bioavailable Inhibitors against Phosphodiesterase-9, a Novel Target for the Treatment of Vascular Dementia. [PMID:30916555] |
| 13. Zhang, Pei and 7 more authors. 2020-07-15 Design, synthesis and evaluation of pyrazolopyrimidinone derivatives as novel PDE9A inhibitors for treatment of Alzheimer's disease. [PMID:32527553] |
| 14. Wu, Yinuo and 8 more authors. 2020-07-23 Discovery of Novel Selective and Orally Bioavailable Phosphodiesterase-1 Inhibitors for the Efficient Treatment of Idiopathic Pulmonary Fibrosis. [PMID:32603117] |
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