4-(3-chloro-4-methoxybenzylamino)-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

ID: ALA3354282

PubChem CID: 118720074

Max Phase: Preclinical

Molecular Formula: C23H26ClN7O3

Molecular Weight: 483.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CNc2nc(N3CCC(CO)C3)ncc2C(=O)NCc2ncccn2)cc1Cl

Standard InChI:  InChI=1S/C23H26ClN7O3/c1-34-19-4-3-15(9-18(19)24)10-27-21-17(22(33)28-12-20-25-6-2-7-26-20)11-29-23(30-21)31-8-5-16(13-31)14-32/h2-4,6-7,9,11,16,32H,5,8,10,12-14H2,1H3,(H,28,33)(H,27,29,30)

Standard InChI Key:  XQOKKJNLZLOKLR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    0.9936  -11.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902  -12.1968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7044  -12.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4193  -12.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7005  -10.9576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277  -10.9490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1234  -10.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8357   -9.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1349  -12.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1372  -13.4298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8482  -12.1902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5473  -10.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -9.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2554   -8.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5338   -8.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8249   -8.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -8.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843   -8.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9756  -10.1137    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8529  -13.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8553  -14.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416  -15.0754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1436  -15.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8599  -16.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754  -15.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5699  -15.0690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2782  -10.9622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1859  -10.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6285   -9.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0341  -10.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4874  -11.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554  -10.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442  -10.1084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 15 18  1  0
 18 19  1  0
 14 20  1  0
 11 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  1 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 28  1  0
 31 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3354282

   ---

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: 483.96

Molecular Weight (Monoisotopic): 483.1786

AlogP: 2.29

#Rotatable Bonds: 9

Polar Surface Area: 125.39

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.73

CX Basic pKa: 6.59

CX LogP: 2.43

CX LogD: 2.42

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.42

Np Likeness Score: -1.59

References

1. Sakamoto T, Koga Y, Hikota M, Matsuki K, Murakami M, Kikkawa K, Fujishige K, Kotera J, Omori K, Morimoto H, Yamada K..  (2014)  The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.,  24  (23): [PMID:25455484] [10.1016/j.bmcl.2014.10.008]

Source

Source(1):

• Scientific Literature