(E)-1-(5-hydroxy-2,2-dimethyl-2H-chroman-6-yl)-3-(3-trifluoromethylphenyl)-propenone

ID: ALA3359428

PubChem CID: 118723525

Max Phase: Preclinical

Molecular Formula: C21H17F3O3

Molecular Weight: 374.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C=Cc2c(ccc(C(=O)/C=C/c3cccc(C(F)(F)F)c3)c2O)O1

Standard InChI:  InChI=1S/C21H17F3O3/c1-20(2)11-10-16-18(27-20)9-7-15(19(16)26)17(25)8-6-13-4-3-5-14(12-13)21(22,23)24/h3-12,26H,1-2H3/b8-6+

Standard InChI Key:  UTGQMDOHYHWACS-SOFGYWHQSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    1.4676  -21.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6426  -21.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0540  -21.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676  -20.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761  -21.6660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761  -20.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886  -20.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870  -21.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5986  -21.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122  -21.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3098  -20.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977  -20.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5957  -19.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236  -20.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7399  -20.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210  -19.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536  -20.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1700  -20.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1686  -21.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8767  -21.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5928  -21.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5922  -20.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8754  -20.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3073  -20.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0223  -20.4213    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.3075  -19.1816    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.0163  -19.5890    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  1  1  0
  4  6  2  0
  1  5  1  0
  5  8  1  0
  7  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 23  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359428

   ---

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: 374.36

Molecular Weight (Monoisotopic): 374.1130

AlogP: 5.49

#Rotatable Bonds: 3

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.06

CX Basic pKa: ┄

CX LogP: 6.02

CX LogD: 5.52

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: 0.96

References

1. Wang L, Chen G, Lu X, Wang S, Han S, Li Y, Ping G, Jiang X, Li H, Yang J, Wu C..  (2015)  Novel chalcone derivatives as hypoxia-inducible factor (HIF)-1 inhibitor: synthesis, anti-invasive and anti-angiogenic properties.,  89  [PMID:25462229] [10.1016/j.ejmech.2014.10.036]

Source

Source(1):

• Scientific Literature