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

ID: ALA4091213

PubChem CID: 137644991

Max Phase: Preclinical

Molecular Formula: C24H22ClN5O2S

Molecular Weight: 479.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(N)=N\C(=N/S(=O)(=O)c1ccccc1)N1CC(c2ccccc2)C(c2ccc(Cl)cc2)=N1

Standard InChI:  InChI=1S/C24H22ClN5O2S/c1-17(26)27-24(29-33(31,32)21-10-6-3-7-11-21)30-16-22(18-8-4-2-5-9-18)23(28-30)19-12-14-20(25)15-13-19/h2-15,22H,16H2,1H3,(H2,26,27,29)

Standard InChI Key:  YBHCEYFNGPBHFI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    6.0092  -15.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239  -14.7879    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339  -14.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7600  -12.3221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4400  -12.7754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0824  -12.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7981  -11.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826  -11.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4720  -13.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7809  -14.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1952  -13.9725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0577  -13.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3666  -14.0835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9505  -15.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9795  -15.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7019  -16.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3940  -15.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3591  -15.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6363  -14.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785  -10.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7818  -10.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756   -9.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661   -9.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654  -10.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6734  -11.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2470  -10.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0636  -10.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5156  -10.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1523   -9.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323   -9.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8839  -10.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9583   -8.9750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0256  -12.8309    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
 12 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091213

   ---

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: 479.99

Molecular Weight (Monoisotopic): 479.1183

AlogP: 4.27

#Rotatable Bonds: 4

Polar Surface Area: 100.48

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.85

CX LogP: 3.89

CX LogD: 3.32

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -0.83

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