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

ID: ALA2413481

PubChem CID: 71769939

Max Phase: Preclinical

Molecular Formula: C19H18O4

Molecular Weight: 310.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(O)=C/C(=O)c2ccccc2)cc(OC)c1

Standard InChI:  InChI=1S/C19H18O4/c1-22-17-10-14(11-18(13-17)23-2)8-9-16(20)12-19(21)15-6-4-3-5-7-15/h3-13,20H,1-2H3/b9-8+,16-12-

Standard InChI Key:  XKXUXEBKBLYQCQ-YCBPJFTGSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    1.3485   -7.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474   -8.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0621   -8.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786   -8.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7756   -7.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0603   -7.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4886   -7.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045   -7.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9174   -7.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6335   -7.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9143   -6.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3463   -7.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0623   -7.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3432   -6.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -8.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7777   -8.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4915   -8.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4857   -7.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7700   -7.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619   -9.6939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340   -7.2165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338   -6.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474  -10.1062    0.0000 C   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
  1 21  1  0
 21 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2413481

   (1Z,4E)-5-(3,5-dimethoxyphenyl)-1-hydroxy-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: 310.35

Molecular Weight (Monoisotopic): 310.1205

AlogP: 4.04

#Rotatable Bonds: 6

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.23

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.38

Np Likeness Score: 0.35

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