4E-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-1-phenylpenta-2,4-dien-1-one

ID: ALA2413479

PubChem CID: 6312255

Max Phase: Preclinical

Molecular Formula: C18H16O4

Molecular Weight: 296.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(O)=C/C(=O)c2ccccc2)ccc1O

Standard InChI:  InChI=1S/C18H16O4/c1-22-18-11-13(8-10-16(18)20)7-9-15(19)12-17(21)14-5-3-2-4-6-14/h2-12,19-20H,1H3/b9-7+,15-12-

Standard InChI Key:  CWEQSIARJVEKSL-QNQPVOBRSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   13.8484   -2.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8472   -2.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5621   -3.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2786   -2.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2756   -2.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5603   -1.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9886   -1.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7045   -2.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4175   -1.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1334   -2.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4143   -0.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8464   -1.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5624   -2.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8433   -0.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5627   -2.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2778   -3.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9917   -2.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9859   -2.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2701   -1.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5619   -4.2069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8473   -4.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1325   -3.3809    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  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 13  1  0
  3 20  1  0
 20 21  1  0
  2 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2413479

   (1Z,4E)-1-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-1-phenylpenta-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: 296.32

Molecular Weight (Monoisotopic): 296.1049

AlogP: 3.74

#Rotatable Bonds: 5

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.03

CX Basic pKa: ┄

CX LogP: 3.29

CX LogD: 3.28

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: 0.71

References

1. Caldarelli A, Penucchini E, Caprioglio D, Genazzani AA, Minassi A..  (2013)  Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids.,  21  (17): [PMID:23830698] [10.1016/j.bmc.2013.05.053]

Source

Source(1):

• Scientific Literature