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

ID: ALA4088079

PubChem CID: 137641597

Max Phase: Preclinical

Molecular Formula: C25H21ClF3N5O2S

Molecular Weight: 547.99

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H21ClF3N5O2S/c1-16(30)31-24(33-37(35,36)21-13-9-19(10-14-21)25(27,28)29)34-15-22(17-5-3-2-4-6-17)23(32-34)18-7-11-20(26)12-8-18/h2-14,22H,15H2,1H3,(H2,30,31,33)

Standard InChI Key:  NLXIJZHFEOSWPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   25.5187  -16.2943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7333  -15.5060    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.9433  -15.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2694  -13.0403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9494  -13.4935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5918  -12.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3075  -12.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4920  -12.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9814  -14.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2903  -14.7461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   23.5671  -14.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8760  -14.8017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4599  -15.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4889  -16.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2113  -17.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.7850  -10.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.6748  -11.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1829  -11.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7564  -11.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5730  -11.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0250  -10.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6617  -10.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8417  -10.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3933  -10.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4677   -9.6931    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.5350  -13.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6271  -17.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6603  -17.8438    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.3177  -16.5904    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.3322  -17.4334    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  5  1  0
  5  6  1  0
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  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
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  2 14  1  0
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 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
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 27 28  1  0
 28 29  2  0
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 30 31  2  0
 31 26  1  0
  7 26  1  0
 23 32  1  0
 12 33  1  0
 17 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088079

   ---

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: 547.99

Molecular Weight (Monoisotopic): 547.1057

AlogP: 5.28

#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: 4.77

CX LogD: 4.20

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.35

Np Likeness Score: -1.00

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