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

ID: ALA4104443

PubChem CID: 137657644

Max Phase: Preclinical

Molecular Formula: C24H21ClIN5O2S

Molecular Weight: 605.89

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H21ClIN5O2S/c1-16(27)28-24(30-34(32,33)21-13-11-20(26)12-14-21)31-15-22(17-5-3-2-4-6-17)23(29-31)18-7-9-19(25)10-8-18/h2-14,22H,15H2,1H3,(H2,27,28,30)

Standard InChI Key:  SBTNHBPBMKICGR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   25.6095  -24.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8241  -23.2363    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.0341  -23.4446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3602  -20.7706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0402  -21.2238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6826  -20.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3983  -19.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5828  -19.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0722  -22.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3811  -22.4764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7954  -22.4209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6579  -22.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9668  -22.5320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5507  -23.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5797  -24.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3021  -24.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9942  -24.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9593  -23.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2366  -23.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0787  -19.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3820  -18.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8758  -17.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0663  -18.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7656  -18.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2737  -19.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8472  -19.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6638  -19.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1158  -18.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7525  -17.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9325  -17.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4841  -18.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5585  -17.4234    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.6258  -21.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7179  -24.7576    0.0000 I   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:

   

   ALA4104443

   ---

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: 605.89

Molecular Weight (Monoisotopic): 605.0149

AlogP: 4.87

#Rotatable Bonds: 4

Polar Surface Area: 100.48

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.85

CX LogP: 4.82

CX LogD: 4.25

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.26

Np Likeness Score: -1.05

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