(R)-1-cyclopentyl-6-((1-morpholino-1-oxopropan-2-yl)amino)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

ID: ALA4544864

PubChem CID: 155553114

Max Phase: Preclinical

Molecular Formula: C17H24N6O3

Molecular Weight: 360.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H](Nc1nc2c(cnn2C2CCCC2)c(=O)[nH]1)C(=O)N1CCOCC1

Standard InChI:  InChI=1S/C17H24N6O3/c1-11(16(25)22-6-8-26-9-7-22)19-17-20-14-13(15(24)21-17)10-18-23(14)12-4-2-3-5-12/h10-12H,2-9H2,1H3,(H2,19,20,21,24)/t11-/m1/s1

Standard InChI Key:  GESQMVSOZXARLD-LLVKDONJSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.8422   -2.7081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8422   -3.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5550   -3.9398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5550   -2.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2637   -2.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2681   -3.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0513   -3.7782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5324   -3.1099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0440   -2.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3158   -4.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8327   -5.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3231   -5.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1068   -5.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1022   -4.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1275   -3.9449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4116   -3.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6970   -3.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4104   -2.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9811   -3.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6982   -4.7723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5550   -1.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9779   -2.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2660   -2.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490   -2.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5482   -3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645   -3.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  7 10  1  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  1
 17 19  1  0
 17 20  2  0
  4 21  2  0
 19 22  1  0
 19 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4544864

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 360.42

Molecular Weight (Monoisotopic): 360.1910

AlogP: 0.89

#Rotatable Bonds: 4

Polar Surface Area: 105.14

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.56

CX Basic pKa: 1.69

CX LogP: 0.12

CX LogD: 0.11

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.84

Np Likeness Score: -1.75

References

1. Wu Y, Zhou Q, Zhang T, Li Z, Chen YP, Zhang P, Yu YF, Geng H, Tian YJ, Zhang C, Wang Y, Chen JW, Chen Y, Luo HB..  (2019)  Discovery of Potent, Selective, and Orally Bioavailable Inhibitors against Phosphodiesterase-9, a Novel Target for the Treatment of Vascular Dementia.,  62  (8): [PMID:30916555] [10.1021/acs.jmedchem.8b01041]

2. Wu Y, Wang Q, Jiang MY, Huang YY, Zhu Z, Han C, Tian YJ, Zhang B, Luo HB..  (2021)  Discovery of Potent Phosphodiesterase-9 Inhibitors for the Treatment of Hepatic Fibrosis.,  64  (13.0): [PMID:34142552] [10.1021/acs.jmedchem.1c00862]

Source

Source(1):

• Scientific Literature