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

ID: ALA2413478

PubChem CID: 71769937

Max Phase: Preclinical

Molecular Formula: C17H14O3

Molecular Weight: 266.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C(O)/C=C/c1ccc(O)cc1)c1ccccc1

Standard InChI:  InChI=1S/C17H14O3/c18-15-9-6-13(7-10-15)8-11-16(19)12-17(20)14-4-2-1-3-5-14/h1-12,18-19H/b11-8+,16-12-

Standard InChI Key:  KVOHGMSNUPHBQV-NJAVVXAXSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   22.7069   -2.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7057   -3.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4205   -3.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1369   -3.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1341   -2.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4187   -2.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8470   -2.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5630   -2.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2760   -2.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9919   -2.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2728   -1.2883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7049   -2.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4209   -2.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7018   -1.2828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4212   -3.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1363   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8502   -3.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8444   -2.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1287   -2.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9909   -3.7767    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
  2 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2413478

   (2z,4e)-5-(4-Hydroxyphenyl)-3-hydroxy-1-phenylpenta-2,4-dien-1-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: 266.30

Molecular Weight (Monoisotopic): 266.0943

AlogP: 3.73

#Rotatable Bonds: 4

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.88

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 3.43

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.38

Np Likeness Score: 0.64

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