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

ID: ALA4442891

PubChem CID: 155516016

Max Phase: Preclinical

Molecular Formula: C16H16ClN5O2

Molecular Weight: 345.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(nc3n2CCN(c2cccc(Cl)c2)C3)n(C)c1=O

Standard InChI:  InChI=1S/C16H16ClN5O2/c1-19-14-13(15(23)20(2)16(19)24)22-7-6-21(9-12(22)18-14)11-5-3-4-10(17)8-11/h3-5,8H,6-7,9H2,1-2H3

Standard InChI Key:  HJXMNEXKEFWFHF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   11.7048   -7.6601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7048   -8.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4101   -8.8818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4101   -7.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1154   -7.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1153   -8.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8935   -8.7313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4097   -9.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9977   -8.8869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4101   -6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9959   -7.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8936   -7.4074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3747   -8.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1832   -7.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5169   -7.2370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0358   -6.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2209   -6.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3297   -7.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8041   -7.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6161   -7.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9496   -6.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4650   -6.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6547   -6.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7951   -5.5719    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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4442891

   ---

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: 345.79

Molecular Weight (Monoisotopic): 345.0993

AlogP: 1.11

#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: ┄

CX LogP: 1.79

CX LogD: 1.79

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -1.77

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