6-(4-Chlorobenzyl)-9-((tetrahydro-2H-pyran-4-yl)methyl)-8,9,10,11-tetrahydropyrido[4',3':4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

ID: ALA4090245

PubChem CID: 72706193

Max Phase: Preclinical

Molecular Formula: C23H24ClN5O2S

Molecular Weight: 470.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1n(Cc2ccc(Cl)cc2)c2sc3c(c2c2ncnn12)CCN(CC1CCOCC1)C3

Standard InChI:  InChI=1S/C23H24ClN5O2S/c24-17-3-1-15(2-4-17)12-28-22-20(21-25-14-26-29(21)23(28)30)18-5-8-27(13-19(18)32-22)11-16-6-9-31-10-7-16/h1-4,14,16H,5-13H2

Standard InChI Key:  IDTOXCSJPHTASJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
   11.9395  -19.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6418  -20.0514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6364  -20.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9248  -21.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2184  -20.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2278  -20.0362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4231  -19.8055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8964  -20.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4094  -21.1278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7449  -22.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9290  -22.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6070  -21.3910    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5905  -22.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2181  -22.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8755  -23.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0637  -23.5525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9490  -18.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7211  -24.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4835  -25.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0102  -24.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1944  -24.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8559  -25.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3291  -26.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1409  -26.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5256  -19.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5350  -18.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2467  -18.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2562  -17.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5539  -17.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8422  -17.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8328  -18.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5634  -16.3515    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  8  9  1  0
  2  7  1  0
  3  9  2  0
 10 11  2  0
 11 12  1  0
 14 15  1  0
 15 16  1  0
 13 16  1  0
 10 14  1  0
 11 13  1  0
  4 10  1  0
  5 12  1  0
  1 17  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 19 24  1  0
 18 21  1  0
 16 18  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 26 31  2  0
 29 32  1  0
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090245

   US10092575, Example 105

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

Calculated Properties

Molecular Weight: 470.00

Molecular Weight (Monoisotopic): 469.1339

AlogP: 3.59

#Rotatable Bonds: 4

Polar Surface Area: 64.66

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.46

CX LogP: 3.91

CX LogD: 3.57

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.88

References

1. Dyck B, Branstetter B, Gharbaoui T, Hudson AR, Breitenbucher JG, Gomez L, Botrous I, Marrone T, Barido R, Allerston CK, Cedervall EP, Xu R, Sridhar V, Barker R, Aertgeerts K, Schmelzer K, Neul D, Lee D, Massari ME, Andersen CB, Sebring K, Zhou X, Petroski R, Limberis J, Augustin M, Chun LE, Edwards TE, Peters M, Tabatabaei A..  (2017)  Discovery of Selective Phosphodiesterase 1 Inhibitors with Memory Enhancing Properties.,  60  (8): [PMID:28406621] [10.1021/acs.jmedchem.7b00302]

Source

Source(1):

• Scientific Literature