10-(2-(1H-Indol-3-yl)ethyl)-1,3-dimethyl-7,8,9,10-tetrahydro-1H-[1,3]diazepino[2,1-f]purine-2,4(3H,6H)-dione

ID: ALA4758188

PubChem CID: 162656142

Max Phase: Preclinical

Molecular Formula: C21H24N6O2

Molecular Weight: 392.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(nc3n2CCCCN3CCc2c[nH]c3ccccc23)n(C)c1=O

Standard InChI:  InChI=1S/C21H24N6O2/c1-24-18-17(19(28)25(2)21(24)29)27-11-6-5-10-26(20(27)23-18)12-9-14-13-22-16-8-4-3-7-15(14)16/h3-4,7-8,13,22H,5-6,9-12H2,1-2H3

Standard InChI Key:  XKPHBCFXKXEQEO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   15.2873   -2.7652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2873   -3.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9925   -3.9869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9925   -2.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6978   -2.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7023   -3.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4775   -3.8261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9925   -1.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5801   -3.9921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9930   -4.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5784   -2.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9473   -3.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4725   -2.5118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6850   -1.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7587   -3.1973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4261   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2898   -2.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1390   -1.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0830   -3.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8947   -4.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2190   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8049   -5.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3451   -6.1044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0185   -4.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0914   -5.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8282   -6.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4926   -5.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4155   -4.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6785   -4.4987    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 12  2  0
 13  5  1  0
  4  8  2  0
  2  9  2  0
  3 10  1  0
  1 11  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 14 16  1  0
 15 17  1  0
 16 18  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 25  1  0
 24 21  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
M  END

Alternative Forms

1. Parent:

   

   ALA4758188

   ---

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: 392.46

Molecular Weight (Monoisotopic): 392.1961

AlogP: 1.76

#Rotatable Bonds: 3

Polar Surface Area: 80.85

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -1.15

References

1. Schoeder CT,Mahardhika AB,Drabczyńska A,Kieć-Kononowicz K,Müller CE.  (2020)  Discovery of Tricyclic Xanthines as Agonists of the Cannabinoid-Activated Orphan G-Protein-Coupled Receptor GPR18.,  11  (10): [PMID:33062188] [10.1021/acsmedchemlett.0c00208]

Source

Source(1):

• Scientific Literature