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

ID: ALA4093905

PubChem CID: 137653051

Max Phase: Preclinical

Molecular Formula: C24H21Cl2N5O2S

Molecular Weight: 514.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(N)=N\C(=N/S(=O)(=O)c1ccc(Cl)cc1)N1C[C@H](c2ccccc2)C(c2ccc(Cl)cc2)=N1

Standard InChI:  InChI=1S/C24H21Cl2N5O2S/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)/t22-/m1/s1

Standard InChI Key:  GZPQTZIUWCQXCF-JOCHJYFZSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   14.0272   -9.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4505   -9.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0762   -9.8742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3525   -4.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5026   -4.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8350   -8.3098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5009   -7.0442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2549   -3.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8138   -6.5863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7202   -9.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2930   -9.0777    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.0565  -10.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0032   -4.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8629   -5.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7450   -3.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2679   -5.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1042   -7.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3115   -2.9821    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.4857  -10.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5713   -3.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1500   -6.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7864  -10.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8507   -4.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0849   -3.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0947   -5.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5333   -7.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2640   -8.2538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0388   -5.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2169  -10.6148    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.4059   -8.3660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7866   -5.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6086   -5.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4948   -9.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0721   -7.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16 25  2  0
 20 15  2  0
  5 24  2  0
 32 13  2  0
 17 30  1  0
 23 16  1  0
  4 31  2  0
 12 22  1  0
  7 26  1  0
 25  5  1  0
 26 27  2  0
 28 32  1  0
 13 20  1  0
 22 19  2  0
  8 23  2  0
  2 10  2  0
 33 11  2  0
 14 16  1  1
  9  7  1  0
 26  6  1  0
 11  3  2  0
 10  1  1  0
 19 29  1  0
 27 11  1  0
 15 18  1  0
  1 12  2  0
 14 28  1  0
  6 17  2  0
 28  9  2  0
 21 14  1  0
 19  2  1  0
  7 21  1  0
 31 32  1  0
 24  8  1  0
 15  4  1  0
 11  1  1  0
 17 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093905

   ---

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: 514.44

Molecular Weight (Monoisotopic): 513.0793

AlogP: 4.92

#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: 4.50

CX LogD: 3.93

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: -0.79

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