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

ID: ALA4474165

PubChem CID: 155537001

Max Phase: Preclinical

Molecular Formula: C16H20N6O2

Molecular Weight: 328.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(nc3n2CCN(CCn2cccc2)C3)n(C)c1=O

Standard InChI:  InChI=1S/C16H20N6O2/c1-18-14-13(15(23)19(2)16(18)24)22-10-9-21(11-12(22)17-14)8-7-20-5-3-4-6-20/h3-6H,7-11H2,1-2H3

Standard InChI Key:  NSQNWVPBSQYBSI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    3.1945  -18.9068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1945  -19.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998  -20.1285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998  -18.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6050  -18.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6050  -19.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3832  -19.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993  -20.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874  -20.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998  -17.6769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4856  -18.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3832  -18.6541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8644  -19.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6729  -19.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0066  -18.4837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5254  -17.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7106  -17.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8193  -18.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2993  -19.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1121  -18.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6579  -19.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4046  -19.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3196  -18.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5203  -18.2633    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
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474165

   ---

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: 328.38

Molecular Weight (Monoisotopic): 328.1648

AlogP: -0.25

#Rotatable Bonds: 3

Polar Surface Area: 69.99

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.60

CX LogP: 0.40

CX LogD: 0.34

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -1.49

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