8-(2,4-Dichlorophenethyl)-1,3-dimethyl-6,7,8,9-tetrahydropyrazino[2,1-f]purine-2,4-(1H,3H)-dione

ID: ALA4474238

PubChem CID: 155537023

Max Phase: Preclinical

Molecular Formula: C18H19Cl2N5O2

Molecular Weight: 408.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(nc3n2CCN(CCc2ccc(Cl)cc2Cl)C3)n(C)c1=O

Standard InChI:  InChI=1S/C18H19Cl2N5O2/c1-22-16-15(17(26)23(2)18(22)27)25-8-7-24(10-14(25)21-16)6-5-11-3-4-12(19)9-13(11)20/h3-4,9H,5-8,10H2,1-2H3

Standard InChI Key:  LOIDJPMSQHLMTM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   24.2722  -12.2661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2722  -13.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9775  -13.4878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9775  -11.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6828  -12.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6828  -13.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4609  -13.3372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9771  -14.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5651  -13.4929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9775  -11.0362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5633  -11.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4610  -12.0134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9421  -12.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7506  -12.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0843  -11.8430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6032  -11.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7883  -11.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8971  -11.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3771  -12.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1898  -12.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6677  -12.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4797  -12.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8132  -12.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3286  -11.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5183  -11.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0356  -10.9296    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.6259  -12.0782    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
  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  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 25 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474238

   ---

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: 408.29

Molecular Weight (Monoisotopic): 407.0916

AlogP: 1.80

#Rotatable Bonds: 3

Polar Surface Area: 65.06

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.78

CX LogP: 2.52

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.62

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