(S)-N-benzyl-1-(2-nitrobenzyl)-5-oxopyrrolidine-2-carboximidamide hydrochloride

ID: ALA4537566

PubChem CID: 155548137

Max Phase: Preclinical

Molecular Formula: C19H21ClN4O3

Molecular Weight: 352.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.N=C(NCc1ccccc1)[C@@H]1CCC(=O)N1Cc1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C19H20N4O3.ClH/c20-19(21-12-14-6-2-1-3-7-14)17-10-11-18(24)22(17)13-15-8-4-5-9-16(15)23(25)26;/h1-9,17H,10-13H2,(H2,20,21);1H/t17-;/m0./s1

Standard InChI Key:  CBGDSLZXTGQTHE-LMOVPXPDSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   43.1914   -4.3914    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   37.7338   -3.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7327   -4.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4407   -4.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1504   -4.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1476   -3.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4389   -3.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8537   -3.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5630   -3.5941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6506   -4.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4506   -4.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8565   -3.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3074   -3.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0451   -4.9547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.4738   -2.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2499   -2.2024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.8641   -1.9142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8595   -2.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6356   -2.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2411   -3.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0166   -2.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1836   -1.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5690   -1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7959   -1.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4350   -2.3713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7261   -1.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1415   -1.9606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 10 14  2  0
 13 15  1  6
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 25 26  2  0
 25 27  1  0
  7 25  1  0
M  CHG  2  25   1  27  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 352.39

Molecular Weight (Monoisotopic): 352.1535

AlogP: 2.85

#Rotatable Bonds: 6

Polar Surface Area: 99.33

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.31

CX LogP: 2.26

CX LogD: -0.03

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.36

Np Likeness Score: -0.92

References

1. Zhang L, Quan J, Zhao Y, Yang D, Zhao Q, Liu P, Cheng M, Ma C..  (2019)  Design, synthesis and biological evaluation of 1-benzyl-5-oxopyrrolidine-2-carboximidamide derivatives as novel neuroprotective agents.,  182  [PMID:31494474] [10.1016/j.ejmech.2019.111654]

Source

Source(1):

• Scientific Literature