N-(1-Amino-2,2-dimethylpropylidene)-3-(4-chlorophenyl)-N'-((4-chlorophenyl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide

ID: ALA4103682

PubChem CID: 137658392

Max Phase: Preclinical

Molecular Formula: C27H27Cl2N5O2S

Molecular Weight: 556.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H27Cl2N5O2S/c1-27(2,3)25(30)31-26(33-37(35,36)22-15-13-21(29)14-16-22)34-17-23(18-7-5-4-6-8-18)24(32-34)19-9-11-20(28)12-10-19/h4-16,23H,17H2,1-3H3,(H2,30,31,33)

Standard InChI Key:  PMKIBLHYLBPREW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   23.6573   -7.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8719   -6.7480    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.0819   -6.9563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4080   -4.2823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0880   -4.7355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7304   -4.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4462   -3.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6306   -3.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1200   -5.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4289   -5.9881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8432   -5.9326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7057   -5.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0146   -6.0437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5985   -7.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6276   -7.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3499   -8.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0420   -7.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0072   -7.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2844   -6.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1265   -2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4298   -2.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9236   -1.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1141   -1.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8134   -2.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3215   -2.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8950   -2.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7116   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1637   -2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8003   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9803   -1.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5319   -2.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6063   -0.9351    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.7657   -8.2694    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.2924   -4.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6996   -4.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4752   -4.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8796   -4.1850    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
 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
 17 33  1  0
 12 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103682

   ---

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: 556.52

Molecular Weight (Monoisotopic): 555.1263

AlogP: 5.95

#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: 7.79

CX LogP: 6.30

CX LogD: 5.77

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.32

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