(1E,4E)-1-(4-Hydroxy-3-methoxyphenyl)-5-(2-nitrophenyl)penta-1,4-dien-3-one

ID: ALA3740450

PubChem CID: 127039794

Max Phase: Preclinical

Molecular Formula: C18H15NO5

Molecular Weight: 325.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)/C=C/c2ccccc2[N+](=O)[O-])ccc1O

Standard InChI:  InChI=1S/C18H15NO5/c1-24-18-12-13(7-11-17(18)21)6-9-15(20)10-8-14-4-2-3-5-16(14)19(22)23/h2-12,21H,1H3/b9-6+,10-8+

Standard InChI Key:  ACDAUZLYGRSMHE-OAMUUVBCSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    3.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856   -8.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -9.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769  -10.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4785   -9.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837   -8.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -7.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8239   -8.1282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7939   -6.3231    0.0000 O   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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
 13 14  1  0
  9 13  1  0
 10 15  1  0
  5  7  1  0
  1 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  2  0
 22 24  1  0
 21 22  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3740450

   ---

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: 325.32

Molecular Weight (Monoisotopic): 325.0950

AlogP: 3.60

#Rotatable Bonds: 6

Polar Surface Area: 89.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: 4.30

CX LogD: 4.30

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: -0.09

References

1. Wang Z, Zou P, Li C, He W, Xiao B, Fang Q, Chen W, Zheng S, Zhao Y, Cai Y, Liang G.  (2015)  Synthesis and biological evaluation of novel semi-conservative monocarbonyl analogs of curcumin as anti-inflammatory agents,  6  (7): [10.1039/C5MD00114E]

2. Rodrigues FC, Anil Kumar NV, Thakur G..  (2019)  Developments in the anticancer activity of structurally modified curcumin: An up-to-date review.,  177  [PMID:31129455] [10.1016/j.ejmech.2019.04.058]

Source

Source(1):

• Scientific Literature