(3E,5E)-3-(2-fluorobenzylidene)-5-(3-hydroxy-4-methoxybenzylidene)dihydro-2H-pyran-4(3H)-one

ID: ALA4099950

PubChem CID: 137662122

Max Phase: Preclinical

Molecular Formula: C20H17FO4

Molecular Weight: 340.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\COC/C(=C\c3ccccc3F)C2=O)cc1O

Standard InChI:  InChI=1S/C20H17FO4/c1-24-19-7-6-13(9-18(19)22)8-15-11-25-12-16(20(15)23)10-14-4-2-3-5-17(14)21/h2-10,22H,11-12H2,1H3/b15-8+,16-10+

Standard InChI Key:  ZOMFXYCYSZLXPS-FAYHMPLTSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.5111  -11.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5111  -12.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163  -12.8522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9216  -12.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9216  -11.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163  -11.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163  -10.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022  -11.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957  -11.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6305  -11.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3370  -11.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873  -11.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813  -11.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6833  -12.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3971  -12.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1002  -12.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3331  -12.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0387  -12.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7486  -12.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7484  -11.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0421  -11.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866  -10.4079    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.4559  -11.2265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4557  -12.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4544  -13.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  1  8  2  0
  8  9  1  0
  5 10  2  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  9  1  0
 11 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 11  1  0
 12 22  1  0
 20 23  1  0
 19 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099950

   ---

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: 340.35

Molecular Weight (Monoisotopic): 340.1111

AlogP: 3.61

#Rotatable Bonds: 3

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.82

CX Basic pKa: ┄

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: -0.26

References

1. Wu J, Wu S, Shi L, Zhang S, Ren J, Yao S, Yun D, Huang L, Wang J, Li W, Wu X, Qiu P, Liang G..  (2017)  Design, synthesis, and evaluation of asymmetric EF24 analogues as potential anti-cancer agents for lung cancer.,  125  [PMID:27886548] [10.1016/j.ejmech.2016.10.027]

Source

Source(1):

• Scientific Literature