ID: ALA3693839
PubChem CID: 135912136
Max Phase: Preclinical
Molecular Formula: C21H20N4O3
Molecular Weight: 376.42
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: O=c1[nH]c(Cc2ccccc2-c2ccco2)nc2c1cnn2C1CCOCC1
Standard InChI: InChI=1S/C21H20N4O3/c26-21-17-13-22-25(15-7-10-27-11-8-15)20(17)23-19(24-21)12-14-4-1-2-5-16(14)18-6-3-9-28-18/h1-6,9,13,15H,7-8,10-12H2,(H,23,24,26)
Standard InChI Key: IFLKCBJJGCYSET-UHFFFAOYSA-N
Molfile:
RDKit 2D
28 32 0 0 0 0 0 0 0 0999 V2000
2.3383 -1.3500 0.0000 O 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 N 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
0.0000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3114 -2.9665 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
-2.4133 -1.7530 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-3.8813 -1.4408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.9619 -2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.4014 -2.0524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.7561 -0.5949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-5.6713 0.4410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.2318 0.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0031 3.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.3039 3.7494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.6005 2.9949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.9021 3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.9073 5.2404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.6108 5.9949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.3092 5.2494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0121 6.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3424 5.3901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.3404 6.5099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5839 7.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.1183 7.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
3 4 1 0
4 5 2 0
5 6 1 0
6 7 2 0
7 2 1 0
7 8 1 0
8 9 2 0
9 10 1 0
10 6 1 0
10 11 1 0
11 12 1 0
12 13 1 0
13 14 1 0
14 15 1 0
15 16 1 0
16 11 1 0
4 17 1 0
17 18 1 0
18 19 2 0
19 20 1 0
20 21 2 0
21 22 1 0
22 23 2 0
23 18 1 0
23 24 1 0
24 25 1 0
25 26 1 0
26 27 2 0
27 28 1 0
28 24 2 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: 376.42 | Molecular Weight (Monoisotopic): 376.1535 | AlogP: 3.32 | #Rotatable Bonds: 4 |
| Polar Surface Area: 85.94 | 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: 0.19 | CX LogP: 1.79 | CX LogD: 1.79 |
| Aromatic Rings: 4 | Heavy Atoms: 28 | QED Weighted: 0.59 | Np Likeness Score: -1.47 |
| 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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