1,3-Dimethyl-8-((2-(thiophen-2-yl)thiazol-4-yl)methyl)-6,7,8,9-tetrahydropyra-zino[2,1-f]purine-2,4(1H,3H)-dione

ID: ALA4540395

PubChem CID: 132578493

Max Phase: Preclinical

Molecular Formula: C18H18N6O2S2

Molecular Weight: 414.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(nc3n2CCN(Cc2csc(-c4cccs4)n2)C3)n(C)c1=O

Standard InChI:  InChI=1S/C18H18N6O2S2/c1-21-15-14(17(25)22(2)18(21)26)24-6-5-23(9-13(24)20-15)8-11-10-28-16(19-11)12-4-3-7-27-12/h3-4,7,10H,5-6,8-9H2,1-2H3

Standard InChI Key:  YQRZRTIMIDGUQW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   12.8522   -2.6002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8522   -3.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5575   -3.8218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5575   -2.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2628   -2.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2627   -3.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0409   -3.6713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5570   -4.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1451   -3.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5575   -1.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1433   -2.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0409   -2.3474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5221   -3.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3306   -2.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6643   -2.1770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1831   -1.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3683   -1.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4770   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9571   -2.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7016   -3.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3625   -4.0060    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0239   -3.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7716   -2.7487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7982   -3.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0504   -4.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8676   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1205   -3.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4595   -3.2966    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7 13  2  0
 12  5  1  0
  3  8  1  0
  2  9  2  0
  4 10  2  0
  1 11  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540395

   ---

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: 414.52

Molecular Weight (Monoisotopic): 414.0933

AlogP: 1.63

#Rotatable Bonds: 3

Polar Surface Area: 77.95

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.25

CX LogP: 1.56

CX LogD: 1.56

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -2.24

References

1. Brunschweiger A, Koch P, Schlenk M, Rafehi M, Radjainia H, Küppers P, Hinz S, Pineda F, Wiese M, Hockemeyer J, Heer J, Denonne F, Müller CE..  (2016)  8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors.,  24  (21): [PMID:27658798] [10.1016/j.bmc.2016.09.003]

Source

Source(1):

• Scientific Literature