3-[(E)-2-(3,5-Dimethoxy-phenyl)-vinyl]-phenol

ID: ALA175736

PubChem CID: 11368874

Max Phase: Preclinical

Molecular Formula: C16H16O3

Molecular Weight: 256.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/c2cccc(O)c2)cc(OC)c1

Standard InChI:  InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)7-6-12-4-3-5-14(17)8-12/h3-11,17H,1-2H3/b7-6+

Standard InChI Key:  KEOJBLYDMOASAY-VOTSOKGWSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    0.1542    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167    1.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -2.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958    0.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    2.3333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833   -2.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  5  1  0
  5  8  2  0
  6  7  1  0
  7  3  2  0
  8  3  1  0
  9  2  1  0
 10  9  1  0
 11 10  2  0
 12  6  1  0
 13  5  1  0
 14 11  1  0
 15 16  1  0
 16  9  2  0
 17 15  2  0
 18 13  1  0
 19 12  1  0
  4  6  2  0
 17 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA175736

   3-[(E)-2-(3,5-Dimethoxy-phenyl)-vinyl]-phenol

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: 256.30

Molecular Weight (Monoisotopic): 256.1099

AlogP: 3.58

#Rotatable Bonds: 4

Polar Surface Area: 38.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.92

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.85

Np Likeness Score: 0.35

References

1. Lion CJ, Matthews CS, Stevens MF, Westwell AD..  (2005)  Synthesis, antitumor evaluation, and apoptosis-inducing activity of hydroxylated (E)-stilbenes.,  48  (4): [PMID:15715501] [10.1021/jm049238e]

2. Roberti M, Pizzirani D, Recanatini M, Simoni D, Grimaudo S, Di Cristina A, Abbadessa V, Gebbia N, Tolomeo M..  (2006)  Identification of a terphenyl derivative that blocks the cell cycle in the G0-G1 phase and induces differentiation in leukemia cells.,  49  (10): [PMID:16686543] [10.1021/jm060253o]

3. Albert S, Horbach R, Deising HB, Siewert B, Csuk R..  (2011)  Synthesis and antimicrobial activity of (E) stilbene derivatives.,  19  (17): [PMID:21803587] [10.1016/j.bmc.2011.07.015]

Source

Source(1):

• Scientific Literature