(E)-3-Phenylpropyl 3-(2,5-dihydroxyphenyl)acrylate

ID: ALA4569185

PubChem CID: 155226852

Max Phase: Preclinical

Molecular Formula: C18H18O4

Molecular Weight: 298.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cc(O)ccc1O)OCCCc1ccccc1

Standard InChI:  InChI=1S/C18H18O4/c19-16-9-10-17(20)15(13-16)8-11-18(21)22-12-4-7-14-5-2-1-3-6-14/h1-3,5-6,8-11,13,19-20H,4,7,12H2/b11-8+

Standard InChI Key:  YEVVZBAHSYINRD-DHZHZOJOSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    8.5507  -17.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2686  -17.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9783  -17.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9783  -18.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2711  -18.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5507  -18.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2711  -19.7831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6921  -17.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4099  -17.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1237  -17.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8373  -17.7213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5511  -17.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2690  -17.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9827  -17.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7008  -17.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4148  -17.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1290  -17.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1290  -18.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4174  -18.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7008  -18.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1237  -16.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2686  -16.4854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 15 20  1  0
 10 21  2  0
  2 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4569185

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 298.34

Molecular Weight (Monoisotopic): 298.1205

AlogP: 3.29

#Rotatable Bonds: 6

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.48

CX Basic pKa: ┄

CX LogP: 4.37

CX LogD: 4.36

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.37

Np Likeness Score: 0.58

References

1. Selka A, Doiron JA, Lyons P, Dastous S, Chiasson A, Cormier M, Turcotte S, Surette ME, Touaibia M..  (2019)  Discovery of a novel 2,5-dihydroxycinnamic acid-based 5-lipoxygenase inhibitor that induces apoptosis and may impair autophagic flux in RCC4 renal cancer cells.,  179  [PMID:31260889] [10.1016/j.ejmech.2019.06.060]

2. Murugesan A,Lassalle-Claux G,Hogan L,Vaillancourt E,Selka A,Luiker K,Kim MJ,Touaibia M,Reiman T.  (2020)  Antimyeloma Potential of Caffeic Acid Phenethyl Ester and Its Analogues through Sp1 Mediated Downregulation of IKZF1-IRF4-MYC Axis.,  83  (12.0): [PMID:33210536] [10.1021/acs.jnatprod.0c00350]

Source

Source(1):

• Scientific Literature