4E-3-hydroxy-1-phenyl-5-(3,4,5-trimethoxyphenyl)penta-2,4-dien-1-one

ID: ALA2413476

PubChem CID: 71770063

Max Phase: Preclinical

Molecular Formula: C20H20O5

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(O)=C/C(=O)c2ccccc2)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H20O5/c1-23-18-11-14(12-19(24-2)20(18)25-3)9-10-16(21)13-17(22)15-7-5-4-6-8-15/h4-13,21H,1-3H3/b10-9+,16-13-

Standard InChI Key:  XCHUBOFHPIZATI-ZDHWLGKOSA-N

Molfile:  

     RDKit          2D

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   11.6939   -7.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6928   -8.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4075   -8.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1239   -8.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1210   -7.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4057   -6.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8339   -6.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5500   -7.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2628   -6.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9788   -7.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2597   -6.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6916   -6.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4077   -7.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6885   -6.1034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4079   -8.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1230   -8.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8369   -8.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8311   -7.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1154   -6.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4073   -9.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9779   -8.5972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9793   -6.9456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6928   -9.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2639   -8.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9791   -6.1207    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
  2 21  1  0
  1 22  1  0
 20 23  1  0
 21 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2413476

   (1Z,4E)-1-hydroxy-1-phenyl-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: 340.38

Molecular Weight (Monoisotopic): 340.1311

AlogP: 4.05

#Rotatable Bonds: 7

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.14

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.36

Np Likeness Score: 0.47

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