(E)-3-(4-Phenoxy-phenyl)-acrylic acid

ID: ALA97691

Cas Number: 717910-83-3

PubChem CID: 12636966

Max Phase: Preclinical

Molecular Formula: C15H12O3

Molecular Weight: 240.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)/C=C/c1ccc(Oc2ccccc2)cc1

Standard InChI:  InChI=1S/C15H12O3/c16-15(17)11-8-12-6-9-14(10-7-12)18-13-4-2-1-3-5-13/h1-11H,(H,16,17)/b11-8+

Standard InChI Key:  XWGDODCEQXQAFQ-DHZHZOJOSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    3.0625    1.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292    1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    2.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -0.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792    0.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042    1.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  2  0
  5  7  1  0
  6  3  1  0
  7 13  1  0
  8  1  1  0
  9  5  1  0
 10  6  2  0
 11  6  1  0
 12 10  1  0
 13 11  2  0
 14  9  2  0
 15  9  1  0
 16 15  2  0
 17 14  1  0
 18 16  1  0
 12  7  2  0
 17 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA97691

   2-Propenoic acid, 3-(4-phenoxyphenyl)-

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: 240.26

Molecular Weight (Monoisotopic): 240.0786

AlogP: 3.58

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.44

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 0.24

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.83

Np Likeness Score: 0.03

References

1. Adisakwattana S, Sookkongwaree K, Roengsumran S, Petsom A, Ngamrojnavanich N, Chavasiri W, Deesamer S, Yibchok-anun S..  (2004)  Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition.,  14  (11): [PMID:15125954] [10.1016/j.bmcl.2004.03.037]

2. Watanabe T, Hayashi K, Yoshimatsu S, Sakai K, Takeyama S, Takashima K..  (1980)  Studies of hypolipidemic agents. 1. Synthesis and hypolipidemic activities of alkoxycinnamic acid derivatives.,  23  (1): [PMID:7359513] [10.1021/jm00175a010]

3. Rastija V, Beslo D, Nikolic S.  (2012)  Two-dimensional quantitative structureactivity relationship study on polyphenols as inhibitors of -glucosidase,  21  (12): [10.1007/s00044-011-9938-0]

Source

Source(1):

• Scientific Literature