5-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-N,N,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine

ID: ALA558838

PubChem CID: 16121920

Max Phase: Preclinical

Molecular Formula: C21H28N6O

Molecular Weight: 380.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(Cc2c(C)[nH]c3nc(N(C)C)ncc23)CC1

Standard InChI:  InChI=1S/C21H28N6O/c1-15-17(16-13-22-21(25(2)3)24-20(16)23-15)14-26-9-11-27(12-10-26)18-7-5-6-8-19(18)28-4/h5-8,13H,9-12,14H2,1-4H3,(H,22,23,24)

Standard InChI Key:  ADAZZWTYEBRRHE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.6821   -0.0347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6821   -0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676   -1.2722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676    0.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532   -0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532   -0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686   -1.1146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164   -0.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686    0.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414   -0.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    1.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5934    1.1764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483    1.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553    2.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2073    1.5195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9524    0.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    0.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0143    1.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663    1.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3733    1.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6282    2.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0762    2.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692    2.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966   -1.2722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1111   -0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966   -2.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7172    3.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102    2.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
  1  2  2  0
  5  4  2  0
  6  7  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  8  1  0
  8  9  2  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
  8 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
  9 11  1  0
  2 24  1  0
 24 25  1  0
 11 12  1  0
 24 26  1  0
 12 13  1  0
 23 27  1  0
  2  3  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA558838

   5-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-N,N,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 380.50

Molecular Weight (Monoisotopic): 380.2325

AlogP: 2.66

#Rotatable Bonds: 5

Polar Surface Area: 60.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.67

CX LogP: 3.02

CX LogD: 2.57

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -1.42

References

1. Linz S, Müller J, Hübner H, Gmeiner P, Troschütz R..  (2009)  Design, synthesis and dopamine D4 receptor binding activities of new N-heteroaromatic 5/6-ring Mannich bases.,  17  (13): [PMID:19481941] [10.1016/j.bmc.2009.05.015]

Source

Source(1):

• Scientific Literature