(E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-trifluoromethylphenyl)-propenone

ID: ALA3359425

PubChem CID: 118723522

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/c3ccc(C(F)(F)F)cc3)c2O)O1

Standard InChI:  InChI=1S/C21H17F3O3/c1-20(2)12-11-16-18(27-20)10-8-15(19(16)26)17(25)9-5-13-3-6-14(7-4-13)21(22,23)24/h3-12,26H,1-2H3/b9-5+

Standard InChI Key:  DSYGKEDDWNCOMV-WEVVVXLNSA-N

Molfile:  

     RDKit          2D

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    1.1574   -7.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -7.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830   -6.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -7.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -5.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4049   -6.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4033   -7.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1154   -7.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8294   -7.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8270   -6.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -5.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125   -5.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412   -5.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2580   -6.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5386   -5.1431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9722   -5.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6890   -6.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6876   -7.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3962   -7.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1128   -7.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1122   -6.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3949   -5.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8280   -7.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8275   -8.4382    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5438   -7.1982    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5413   -8.0232    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
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 17 18  1  0
 18 19  1  0
 18 23  2  0
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 20 21  1  0
 21 22  2  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359425

   ---

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: 1.08

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