6-(Benzyl)-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: ALA4069196

PubChem CID: 137631826

Max Phase: Preclinical

Molecular Formula: C23H25N5O2S

Molecular Weight: 435.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1n(Cc2ccccc2)c2sc3c(c2c2ncnn12)CCN(CC1CCOCC1)C3

Standard InChI:  InChI=1S/C23H25N5O2S/c29-23-27(13-16-4-2-1-3-5-16)22-20(21-24-15-25-28(21)23)18-6-9-26(14-19(18)31-22)12-17-7-10-30-11-8-17/h1-5,15,17H,6-14H2

Standard InChI Key:  ANUHVXTXGNXMTG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 36  0  0  0  0  0  0  0  0999 V2000
   11.9472  -19.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6550  -19.6100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6606  -20.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9544  -20.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2466  -20.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2409  -19.6156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4304  -19.3541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9152  -20.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4355  -20.6765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7891  -21.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9752  -21.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6398  -20.9807    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.6460  -22.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2697  -22.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9405  -23.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1307  -23.1352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9415  -18.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8015  -23.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5807  -25.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0960  -24.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2821  -24.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9570  -25.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4375  -25.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2515  -25.8605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5290  -19.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5275  -18.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2338  -17.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2281  -17.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5203  -16.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8141  -17.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8156  -17.9869    0.0000 C   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
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4069196

   ---

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: 435.55

Molecular Weight (Monoisotopic): 435.1729

AlogP: 2.94

#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: 3.30

CX LogD: 2.97

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: -1.77

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