3-Chloro-4-{4-[5-(3-{[glycyl(methyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}benzoic acid dihydrochloride

ID: ALA4063342

PubChem CID: 68107525

Max Phase: Preclinical

Molecular Formula: C25H29Cl3N6O3

Molecular Weight: 494.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(Cc1cccc(-c2cnc(N3CCN(c4ccc(C(=O)O)cc4Cl)CC3)nc2)c1)C(=O)CN.Cl.Cl

Standard InChI:  InChI=1S/C25H27ClN6O3.2ClH/c1-30(23(33)13-27)16-17-3-2-4-18(11-17)20-14-28-25(29-15-20)32-9-7-31(8-10-32)22-6-5-19(24(34)35)12-21(22)26;;/h2-6,11-12,14-15H,7-10,13,16,27H2,1H3,(H,34,35);2*1H

Standard InChI Key:  HWXBGKVIURAJOO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 38  0  0  0  0  0  0  0  0999 V2000
   12.2909  -11.7773    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5447  -13.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2518  -12.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9587  -13.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6659  -12.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6620  -12.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9551  -11.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2479  -12.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336  -12.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5444  -14.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3691  -11.6799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0760  -12.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7831  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7834  -10.8560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0723  -10.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3652  -10.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4905  -10.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1974  -10.8534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9045  -10.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9006   -9.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1896   -9.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4866   -9.6310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6078   -9.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3147   -9.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0218   -9.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0221   -8.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3110   -7.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6039   -8.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7329   -9.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4359   -9.2070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4361   -8.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1469   -9.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4437  -10.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1508  -10.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8540   -9.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3728  -13.3143    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1611  -11.9485    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  2  9  2  0
  2 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 16  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 23 28  2  0
 30 31  1  0
 33 34  1  0
 32 34  1  0
 32 35  2  0
 30 32  1  0
 29 30  1  0
 25 29  1  0
 20 23  1  0
 14 17  1  0
  6 11  1  0
  5 36  1  0
M  END

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: 494.98

Molecular Weight (Monoisotopic): 494.1833

AlogP: 2.74

#Rotatable Bonds: 7

Polar Surface Area: 115.89

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.54

CX Basic pKa: 8.13

CX LogP: 0.47

CX LogD: 0.41

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.51

Np Likeness Score: -1.42

References

1. Yamaki S, Koga Y, Nagashima A, Kondo M, Shimada Y, Kadono K, Moritomo A, Yoshihara K..  (2017)  Synthesis and pharmacological evaluation of glycine amide derivatives as novel vascular adhesion protein-1 inhibitors without CYP3A4 and CYP2C19 inhibition.,  25  (15): [PMID:28601507] [10.1016/j.bmc.2017.05.059]

Source

Source(1):

• Scientific Literature