N-(1-Aminoethylidene)-N'-((4-bromophenyl)sulfonyl)-3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide

ID: ALA4092420

PubChem CID: 137653701

Max Phase: Preclinical

Molecular Formula: C24H21BrClN5O2S

Molecular Weight: 558.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(N)=N\C(=N/S(=O)(=O)c1ccc(Br)cc1)N1CC(c2ccccc2)C(c2ccc(Cl)cc2)=N1

Standard InChI:  InChI=1S/C24H21BrClN5O2S/c1-16(27)28-24(30-34(32,33)21-13-9-19(25)10-14-21)31-15-22(17-5-3-2-4-6-17)23(29-31)18-7-11-20(26)12-8-18/h2-14,22H,15H2,1H3,(H2,27,28,30)

Standard InChI Key:  FWWQASVOENYRCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   34.2684  -24.9120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4830  -24.1237    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.6930  -24.3319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0191  -21.6579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6991  -22.1112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3415  -21.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0573  -20.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2417  -20.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7312  -22.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0400  -23.3638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4543  -23.3082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3168  -22.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6257  -23.4193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2096  -24.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2387  -25.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9610  -25.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6531  -25.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6183  -24.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8955  -24.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7376  -20.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0409  -19.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5347  -18.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7252  -18.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4245  -19.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9326  -20.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5061  -20.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3227  -20.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7748  -19.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4114  -18.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5914  -18.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1430  -19.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2174  -18.3108    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.2848  -22.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3768  -25.6450    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  2  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  2  0
 12 13  1  0
 11  2  1  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  8 20  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
  7 26  1  0
 23 32  1  0
 12 33  1  0
 17 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092420

   ---

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: 558.89

Molecular Weight (Monoisotopic): 557.0288

AlogP: 5.03

#Rotatable Bonds: 4

Polar Surface Area: 100.48

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.85

CX LogP: 4.66

CX LogD: 4.09

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: -0.90

References

1. Iyer MR, Cinar R, Katz A, Gao M, Erdelyi K, Jourdan T, Coffey NJ, Pacher P, Kunos G..  (2017)  Design, Synthesis, and Biological Evaluation of Novel, Non-Brain-Penetrant, Hybrid Cannabinoid CB1R Inverse Agonist/Inducible Nitric Oxide Synthase (iNOS) Inhibitors for the Treatment of Liver Fibrosis.,  60  (3): [PMID:28085283] [10.1021/acs.jmedchem.6b01504]

Source

Source(1):

• Scientific Literature