(1E,4E)-1-(4-Bromo-1-methyl-1H-pyrazol-3-yl)-5-(1-(secbutyl)-1H-imidazol-2-yl)penta-1,4-dien-3-one

ID: ALA4211442

PubChem CID: 145967400

Max Phase: Preclinical

Molecular Formula: C16H19BrN4O

Molecular Weight: 363.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)n1ccnc1/C=C/C(=O)/C=C/c1nn(C)cc1Br

Standard InChI:  InChI=1S/C16H19BrN4O/c1-4-12(2)21-10-9-18-16(21)8-6-13(22)5-7-15-14(17)11-20(3)19-15/h5-12H,4H2,1-3H3/b7-5+,8-6+

Standard InChI Key:  XMXRTQQUMYDHOU-KQQUZDAGSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   18.3463  -16.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3463  -17.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0608  -17.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0608  -18.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3463  -19.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7753  -17.4602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3463  -19.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0138  -20.4202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7588  -21.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9338  -21.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6789  -20.4202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8943  -20.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2812  -20.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4966  -20.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7227  -19.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7387  -15.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5456  -15.4023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6319  -16.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8782  -16.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3262  -15.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4031  -14.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7067  -17.3653    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  3  6  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  7 11  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 11 12  1  0
  5  7  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 16 20  1  0
 16 21  1  0
 19 22  1  0
  1 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4211442

   ---

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: 363.26

Molecular Weight (Monoisotopic): 362.0742

AlogP: 3.65

#Rotatable Bonds: 6

Polar Surface Area: 52.71

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.00

CX LogP: 3.88

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: -0.89

References

1. Zhang X, Guo S, Chen C, Perez GR, Zhang C, Patanapongpibul M, Subrahmanyam N, Wang R, Keith J, Chen G, Dong Y, Zhang Q, Zhong Q, Zheng S, Wang G, Chen QH..  (2017)  Asymmetric 1,5-diarylpenta-1,4-dien-3-ones: Antiproliferative activity in prostate epithelial cell models and pharmacokinetic studies.,  137  [PMID:28601720] [10.1016/j.ejmech.2017.05.062]

Source

Source(1):

• Scientific Literature