6-(4-Chlorobenzyl)-9-(oxetan-3-yl)-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: ALA4084358

PubChem CID: 118485601

Max Phase: Preclinical

Molecular Formula: C20H18ClN5O2S

Molecular Weight: 427.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1n(Cc2ccc(Cl)cc2)c2sc3c(c2c2ncnn12)CCN(C1COC1)C3

Standard InChI:  InChI=1S/C20H18ClN5O2S/c21-13-3-1-12(2-4-13)7-25-19-17(18-22-11-23-26(18)20(25)27)15-5-6-24(8-16(15)29-19)14-9-28-10-14/h1-4,11,14H,5-10H2

Standard InChI Key:  YNHRARXBLWKRFA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 34  0  0  0  0  0  0  0  0999 V2000
   13.1814  -17.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8946  -18.3412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9070  -19.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2062  -19.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4931  -19.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4807  -18.3616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6707  -18.0791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1600  -18.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6851  -19.4013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0434  -20.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349  -20.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8937  -19.7305    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9115  -21.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5369  -21.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2135  -21.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4008  -21.8825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1731  -17.1258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6219  -23.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3797  -23.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0774  -22.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3196  -22.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7676  -17.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7552  -17.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4600  -16.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4476  -15.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7345  -15.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0337  -15.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0420  -16.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7221  -14.6908    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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 21  1  0
 16 20  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 23 28  2  0
 26 29  1  0
  6 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084358

   US10092575, Example 106

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: 427.92

Molecular Weight (Monoisotopic): 427.0870

AlogP: 2.56

#Rotatable Bonds: 3

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: 4.63

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -1.54

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