8-((2-(3-Chlorophenyl)thiazol-4-yl)methyl)-1,3-dimethyl-6,7,8,9-tetrahydro-pyrazino[2,1-f]purine-2,4(1H,3H)-dione

ID: ALA4483392

PubChem CID: 155540615

Max Phase: Preclinical

Molecular Formula: C20H19ClN6O2S

Molecular Weight: 442.93

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(nc3n2CCN(Cc2csc(-c4cccc(Cl)c4)n2)C3)n(C)c1=O

Standard InChI:  InChI=1S/C20H19ClN6O2S/c1-24-17-16(19(28)25(2)20(24)29)27-7-6-26(10-15(27)23-17)9-14-11-30-18(22-14)12-4-3-5-13(21)8-12/h3-5,8,11H,6-7,9-10H2,1-2H3

Standard InChI Key:  JFIAUWNUIUKPBJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   13.2608  -11.7832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2608  -12.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9661  -13.0049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9661  -11.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6713  -11.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6713  -12.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4495  -12.8544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9656  -13.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5537  -13.0101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9661  -10.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5519  -11.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4495  -11.5305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9307  -12.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7392  -12.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0729  -11.3601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5917  -10.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7769  -10.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8856  -11.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3656  -11.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1145  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7754  -13.1905    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.4368  -12.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1845  -11.9332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2139  -12.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3815  -13.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1577  -14.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7662  -13.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5932  -12.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8171  -12.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1987  -12.1148    0.0000 Cl  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
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  4 10  2  0
  1 11  1  0
 12 13  1  0
 12 17  1  0
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 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
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483392

   ---

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: 442.93

Molecular Weight (Monoisotopic): 442.0979

AlogP: 2.23

#Rotatable Bonds: 3

Polar Surface Area: 77.95

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.49

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -2.15

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