4-(4-Methoxyphenyl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-ylamine

ID: ALA494648

PubChem CID: 25129525

Max Phase: Preclinical

Molecular Formula: C16H21N5O

Molecular Weight: 299.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc(N3CCN(C)CC3)nc(N)n2)cc1

Standard InChI:  InChI=1S/C16H21N5O/c1-20-7-9-21(10-8-20)15-11-14(18-16(17)19-15)12-3-5-13(22-2)6-4-12/h3-6,11H,7-10H2,1-2H3,(H2,17,18,19)

Standard InChI Key:  XVSFXGNIAZCOPM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    6.7711   -8.1803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7699   -9.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4845   -9.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2007   -9.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1978   -8.1767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4827   -7.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9132   -9.4173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9125  -10.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6233  -10.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3392  -10.2441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3399   -9.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6247   -9.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0525  -10.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4803   -6.9430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0573   -9.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431   -9.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6291   -9.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280  -10.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3469  -10.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0580  -10.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140  -10.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996  -10.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  4  7  1  0
  6  1  1  0
 10 13  1  0
  7  8  1  0
  6 14  1  0
  1  2  2  0
  3  4  2  0
 15 16  2  0
 16 17  1  0
  4  5  1  0
 17 18  2  0
  2  3  1  0
 18 19  1  0
  5  6  2  0
 19 20  2  0
 20 15  1  0
  2 15  1  0
  7 12  1  0
 18 21  1  0
  8  9  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA494648

   4-(4-Methoxyphenyl)-6-(4-methylpiperazin-1-yl)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: 299.38

Molecular Weight (Monoisotopic): 299.1746

AlogP: 1.49

#Rotatable Bonds: 3

Polar Surface Area: 67.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.64

CX LogP: 2.32

CX LogD: 1.85

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.93

Np Likeness Score: -1.34

References

1. Altenbach RJ, Adair RM, Bettencourt BM, Black LA, Fix-Stenzel SR, Gopalakrishnan SM, Hsieh GC, Liu H, Marsh KC, McPherson MJ, Milicic I, Miller TR, Vortherms TA, Warrior U, Wetter JM, Wishart N, Witte DG, Honore P, Esbenshade TA, Hancock AA, Brioni JD, Cowart MD..  (2008)  Structure-activity studies on a series of a 2-aminopyrimidine-containing histamine H4 receptor ligands.,  51  (20): [PMID:18811133] [10.1021/jm8005959]

2. Schultes S, Nijmeijer S, Engelhardt H, Kooistra AJ, Vischer HF, de Esch IJP, Haaksma EEJ, Leurs R, de Graaf C.  (2013)  Mapping histamine H4receptorligand binding modes,  4  (1): [10.1039/C2MD20212C]

Source

Source(1):

• Scientific Literature