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

ID: ALA4095928

PubChem CID: 137653846

Max Phase: Preclinical

Molecular Formula: C27H28ClN5O2S

Molecular Weight: 522.07

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H28ClN5O2S/c1-18(2)20-11-15-24(16-12-20)36(34,35)32-27(30-19(3)29)33-17-25(21-7-5-4-6-8-21)26(31-33)22-9-13-23(28)14-10-22/h4-16,18,25H,17H2,1-3H3,(H2,29,30,32)

Standard InChI Key:  PLCVQFDHZUZAMO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   14.0491  -16.4016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2637  -15.6133    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.4737  -15.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7998  -13.1476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4798  -13.6008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1222  -13.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8380  -12.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0224  -12.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5119  -14.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8207  -14.8534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2351  -14.7979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0975  -14.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4064  -14.9090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9903  -15.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8216  -10.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3154  -10.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5059  -10.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2052  -11.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7133  -11.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2868  -11.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1034  -11.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5555  -11.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1921  -10.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3721  -10.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9237  -10.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9981   -9.8004    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.0655  -13.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1575  -17.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1907  -17.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8481  -16.6977    0.0000 C   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
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 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
 34 35  1  0
 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095928

   ---

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: 522.07

Molecular Weight (Monoisotopic): 521.1652

AlogP: 5.39

#Rotatable Bonds: 5

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: 5.14

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.36

Np Likeness Score: -0.82

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