6-benzyloxymethyl-5-[4-(4-chloro-benzylamino)-phenyl]-pyrimidine-2,4-diamine

ID: ALA425048

PubChem CID: 11282247

Max Phase: Preclinical

Molecular Formula: C25H24ClN5O

Molecular Weight: 445.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c(-c2ccc(NCc3ccc(Cl)cc3)cc2)c(COCc2ccccc2)n1

Standard InChI:  InChI=1S/C25H24ClN5O/c26-20-10-6-17(7-11-20)14-29-21-12-8-19(9-13-21)23-22(30-25(28)31-24(23)27)16-32-15-18-4-2-1-3-5-18/h1-13,29H,14-16H2,(H4,27,28,30,31)

Standard InChI Key:  YHNPYJODGMGFSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -4.7181    0.6834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7193   -0.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0044   -0.5569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2880   -0.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2909    0.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0062    1.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5779    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647    0.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1523    1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549    1.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8760    2.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5854    1.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4341   -0.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087    1.9211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4426    2.3459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2740    1.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9864    2.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022    1.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4140    2.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4103    3.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6887    3.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798    3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221    3.6013    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8591   -0.1413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -0.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4301   -0.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2837   -0.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9970   -0.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9962    0.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2760    1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344    0.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 10 16  1  0
  7  8  2  0
 16 17  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  2  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
  2  3  2  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
 23 18  1  0
  5  6  1  0
 21 24  1  0
 11 12  2  0
 15 25  1  0
 12  7  1  0
 25 26  1  0
  6  1  2  0
 26 27  1  0
  2 13  1  0
 27 28  2  0
  1  2  1  0
 28 29  1  0
  6 14  1  0
 29 30  2  0
  5  7  1  0
 30 31  1  0
  4 15  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA425048

   6-Benzyloxymethyl-5-[4-(4-chloro-benzylamino)-phenyl]-pyrimidine-2,4-diamine

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: 445.95

Molecular Weight (Monoisotopic): 445.1669

AlogP: 5.29

#Rotatable Bonds: 8

Polar Surface Area: 99.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.95

CX LogP: 4.80

CX LogD: 4.78

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -0.91

References

1. Serby MD, Zhao H, Szczepankiewicz BG, Kosogof C, Xin Z, Liu B, Liu M, Nelson LT, Kaszubska W, Falls HD, Schaefer V, Bush EN, Shapiro R, Droz BA, Knourek-Segel VE, Fey TA, Brune ME, Beno DW, Turner TM, Collins CA, Jacobson PB, Sham HL, Liu G..  (2006)  2,4-diaminopyrimidine derivatives as potent growth hormone secretagogue receptor antagonists.,  49  (8): [PMID:16610800] [10.1021/jm0510934]

2. Xin Z, Serby MD, Zhao H, Kosogof C, Szczepankiewicz BG, Liu M, Liu B, Hutchins CW, Sarris KA, Hoff ED, Falls HD, Lin CW, Ogiela CA, Collins CA, Brune ME, Bush EN, Droz BA, Fey TA, Knourek-Segel VE, Shapiro R, Jacobson PB, Beno DW, Turner TM, Sham HL, Liu G..  (2006)  Discovery and pharmacological evaluation of growth hormone secretagogue receptor antagonists.,  49  (15): [PMID:16854051] [10.1021/jm060461g]

Source

Source(1):

• Scientific Literature