N-(3-{2-[(2R)-2-(Hydroxymethyl)pyrrolidin-1-yl]pyrimidin-5-yl}benzyl)-N-methylglycinamide dihydrochloride

ID: ALA4059576

PubChem CID: 137634929

Max Phase: Preclinical

Molecular Formula: C19H27Cl2N5O2

Molecular Weight: 355.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CC(N)=O)Cc1cccc(-c2cnc(N3CCC[C@@H]3CO)nc2)c1.Cl.Cl

Standard InChI:  InChI=1S/C19H25N5O2.2ClH/c1-23(12-18(20)26)11-14-4-2-5-15(8-14)16-9-21-19(22-10-16)24-7-3-6-17(24)13-25;;/h2,4-5,8-10,17,25H,3,6-7,11-13H2,1H3,(H2,20,26);2*1H/t17-;;/m1../s1

Standard InChI Key:  BFILLIIJBSZIRD-ZEECNFPPSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   10.9899  -11.8800    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.2138   -8.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5160   -9.6738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5085   -8.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2104   -7.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9266   -8.8477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8107  -10.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1020   -9.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3967  -10.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6839   -9.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805   -8.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3858   -8.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0945   -8.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5680  -10.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5646  -10.1156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2699   -9.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9786  -10.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9861  -10.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2767  -11.3349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8627  -11.3438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2247  -10.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125  -11.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5688  -11.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9798  -12.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775  -12.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3860  -12.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2179  -13.5022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9628  -11.9143    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  2  4  1  0
  2  5  2  0
  2  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 14 20  1  0
 10 17  1  0
  3  7  1  0
  3 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 20  1  0
 25 26  1  1
 26 27  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: 355.44

Molecular Weight (Monoisotopic): 355.2008

AlogP: 1.02

#Rotatable Bonds: 7

Polar Surface Area: 95.58

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.29

CX LogP: 0.87

CX LogD: 0.62

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -1.15

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