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

ID: ALA2413477

PubChem CID: 71770064

Max Phase: Preclinical

Molecular Formula: C18H16O5

Molecular Weight: 312.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(O)=C/C(=O)c2ccc(O)cc2)ccc1O

Standard InChI:  InChI=1S/C18H16O5/c1-23-18-10-12(3-9-16(18)21)2-6-15(20)11-17(22)13-4-7-14(19)8-5-13/h2-11,19-21H,1H3/b6-2+,15-11-

Standard InChI Key:  ZIDXREBLPMGOCJ-ZMXQUZCPSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   20.6441   -7.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6430   -8.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3578   -8.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0742   -8.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0713   -7.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3559   -7.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7842   -7.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5002   -7.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2131   -7.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9291   -7.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2100   -6.3882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6420   -7.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3581   -7.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6389   -6.3828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3583   -8.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0735   -8.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7873   -8.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7816   -7.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0658   -7.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5039   -8.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3575   -9.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9281   -8.8766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0719  -10.1152    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
 17 20  1  0
  3 21  1  0
  2 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2413477

   (1Z,4E)-1-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)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: 312.32

Molecular Weight (Monoisotopic): 312.0998

AlogP: 3.44

#Rotatable Bonds: 5

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.80

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 2.83

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.34

Np Likeness Score: 0.86

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