1-(4-methoxyphenyl)-5-(4-nitrophenyl)-1,4-pentadien-3-one

ID: ALA242295

PubChem CID: 872397

Max Phase: Preclinical

Molecular Formula: C18H15NO4

Molecular Weight: 309.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)/C=C/c2ccc([N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C18H15NO4/c1-23-18-12-6-15(7-13-18)5-11-17(20)10-4-14-2-8-16(9-3-14)19(21)22/h2-13H,1H3/b10-4+,11-5+

Standard InChI Key:  YHPCOAIOELXCCP-ZVSIBQGLSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -1.0389  -12.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401  -13.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253  -13.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3912  -13.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883  -12.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3271  -12.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012  -12.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8172  -12.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439  -12.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5274  -12.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5233  -11.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582  -12.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6728  -12.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684  -13.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3821  -13.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0974  -13.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0945  -12.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801  -12.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8146  -13.9524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5284  -13.5387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8160  -14.7774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549  -13.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690  -13.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  9 12  2  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  4  5  1  0
  8 10  1  0
  9 10  1  0
 19 20  2  0
 19 21  1  0
 16 19  1  0
  2  3  1  0
  2 22  1  0
 10 11  2  0
 22 23  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA242295

   (1E,4E)-1-(4-methoxyphenyl)-5-(4-nitrophenyl)penta-1,4-dien-3-one

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: 309.32

Molecular Weight (Monoisotopic): 309.1001

AlogP: 3.90

#Rotatable Bonds: 6

Polar Surface Area: 69.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.61

CX LogD: 4.61

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.46

Np Likeness Score: -0.33

References

1. Das U, Kawase M, Sakagami H, Ideo A, Shimada J, Molnár J, Baráth Z, Bata Z, Dimmock JR..  (2007)  3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: a novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity.,  15  (10): [PMID:17383883] [10.1016/j.bmc.2007.03.022]

Source

Source(1):

• Scientific Literature