4-[(E)-[4-[3-(dimethylamino)propoxy]phenyl]methyleneamino]-1,5-dimethyl-2-phenyl-pyrazol-3-one

ID: ALA5279918

Max Phase: Preclinical

Molecular Formula: C23H28N4O2

Molecular Weight: 392.50

Names and Identifiers

Canonical SMILES:  Cc1c(/N=C/c2ccc(OCCCN(C)C)cc2)c(=O)n(-c2ccccc2)n1C

Standard InChI:  InChI=1S/C23H28N4O2/c1-18-22(23(28)27(26(18)4)20-9-6-5-7-10-20)24-17-19-11-13-21(14-12-19)29-16-8-15-25(2)3/h5-7,9-14,17H,8,15-16H2,1-4H3/b24-17+

Standard InChI Key:  CDGLDERDAXTHBD-JJIBRWJFSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.3331    0.0955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0510   -0.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1440   -1.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356   -1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9523   -1.2954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2942   -2.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3589   -0.5776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1786   -0.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078    0.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3276    0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8180   -0.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4887   -1.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6691   -1.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017    0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666    0.8392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221   -0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956    0.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066   -0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245    0.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314    0.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204    1.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1025    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    1.2916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6848    1.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3891    0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1137    1.2213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8180    0.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1340    2.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 13  8  2  0
 12 13  1  0
 14  7  1  0
  2 14  1  0
 14 15  2  0
  1 16  2  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279918

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 392.50

Molecular Weight (Monoisotopic): 392.2212

AlogP: 3.57

#Rotatable Bonds: 8

Polar Surface Area: 51.76

Molecular Species: BASE

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.26

CX LogP: 2.80

CX LogD: 0.95

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.37

References

1. Zhao Z, Dai X, Li C, Wang X, Tian J, Feng Y, Xie J, Ma C, Nie Z, Fan P, Qian M, He X, Wu S, Zhang Y, Zheng X..  (2020)  Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect.,  186  [PMID:31761383] [10.1016/j.ejmech.2019.111893]

Source

Source(1):

• Scientific Literature