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

ID: ALA4451303

PubChem CID: 132578492

Max Phase: Preclinical

Molecular Formula: C20H23N5O2

Molecular Weight: 365.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(nc3n2CCN([C@@H]2CCCc4ccccc42)C3)n(C)c1=O

Standard InChI:  InChI=1S/C20H23N5O2/c1-22-18-17(19(26)23(2)20(22)27)25-11-10-24(12-16(25)21-18)15-9-5-7-13-6-3-4-8-14(13)15/h3-4,6,8,15H,5,7,9-12H2,1-2H3/t15-/m1/s1

Standard InChI Key:  GEMWFQCNZGPNFF-OAHLLOKOSA-N

Molfile:  

 
     RDKit          2D

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   34.1487   -8.5516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1487   -9.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8540   -9.7733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8540   -8.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5593   -8.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5592   -9.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3374   -9.6227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8535  -10.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4416   -9.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8540   -7.3217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4398   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3374   -8.2989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8186   -8.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6271   -8.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9608   -8.1285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4796   -7.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6648   -7.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7735   -8.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3943   -7.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9153   -7.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0996   -7.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0575   -8.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2505   -8.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9195   -9.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3943  -10.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2040  -10.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5314   -9.2752    0.0000 C   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
 18 15  1  6
 18 23  1  0
 18 21  1  0
 22 19  1  0
 19 20  1  0
 20 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4451303

   ---

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: 365.44

Molecular Weight (Monoisotopic): 365.1852

AlogP: 1.33

#Rotatable Bonds: 1

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: 5.62

CX LogP: 2.01

CX LogD: 2.00

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -0.84

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