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

ID: ALA242294

PubChem CID: 44428794

Max Phase: Preclinical

Molecular Formula: C20H19NO6

Molecular Weight: 369.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)/C=C/c2ccc([N+](=O)[O-])cc2)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H19NO6/c1-25-18-12-15(13-19(26-2)20(18)27-3)7-11-17(22)10-6-14-4-8-16(9-5-14)21(23)24/h4-13H,1-3H3/b10-6+,11-7+

Standard InChI Key:  KBBBTQYITILIOW-JMQWPVDRSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   10.0527   -7.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0516   -8.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7664   -8.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4828   -8.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4800   -7.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7646   -7.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1929   -7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9089   -7.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3355   -7.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6191   -7.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6150   -6.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0499   -7.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7645   -7.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7600   -8.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4738   -8.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1891   -8.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1862   -7.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4718   -7.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9063   -8.8565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6200   -8.4428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9077   -9.6815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3368   -8.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6226   -8.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3382   -7.2210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3380   -6.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7662   -9.6985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0516  -10.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  5  6  2  0
  1 24  1  0
  9 12  2  0
 24 25  1  0
  6  1  1  0
  3 26  1  0
 12 13  1  0
 26 27  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA242294

   (1E,4E)-1-(4-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)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: 369.37

Molecular Weight (Monoisotopic): 369.1212

AlogP: 3.92

#Rotatable Bonds: 8

Polar Surface Area: 87.90

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.40

Np Likeness Score: -0.08

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