2-(3-Fluorophenyl)-4-(3-hydroxyphenyl)-5H-indeno[1,2-b]-pyridin-9-ol

ID: ALA4476855

PubChem CID: 155538577

Max Phase: Preclinical

Molecular Formula: C24H16FNO2

Molecular Weight: 369.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Oc1cccc(-c2cc(-c3cccc(F)c3)nc3c2Cc2cccc(O)c2-3)c1

Standard InChI:  InChI=1S/C24H16FNO2/c25-17-7-1-5-15(10-17)21-13-19(14-4-2-8-18(27)11-14)20-12-16-6-3-9-22(28)23(16)24(20)26-21/h1-11,13,27-28H,12H2

Standard InChI Key:  ZALQNGMCJMLOLB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   34.1273  -10.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1261  -11.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8410  -12.0749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8392  -10.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8338   -9.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5489   -9.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5468   -8.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8304   -7.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1148   -8.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1204   -9.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4131  -12.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6986  -11.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9843  -12.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9831  -12.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7024  -13.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4138  -12.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5546  -10.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5595  -11.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3392  -10.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8290  -11.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3440  -11.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6809  -12.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5025  -12.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9861  -12.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6466  -11.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1973  -13.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7047  -14.1346    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.2603   -7.9467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 18  2  0
 17  4  2  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
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  9 10  2  0
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  4  5  1  0
 11 12  2  0
 12 13  1  0
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 15 16  2  0
 16 11  1  0
  2 11  1  0
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 20 19  1  0
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 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
 15 27  1  0
  7 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476855

   ---

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: 369.39

Molecular Weight (Monoisotopic): 369.1165

AlogP: 5.54

#Rotatable Bonds: 2

Polar Surface Area: 53.35

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.47

CX Basic pKa: 2.89

CX LogP: 6.12

CX LogD: 6.09

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -0.16

References

1. Kadayat TM, Park S, Shrestha A, Jo H, Hwang SY, Katila P, Shrestha R, Nepal MR, Noh K, Kim SK, Koh WS, Kim KS, Jeon YH, Jeong TC, Kwon Y, Lee ES..  (2019)  Discovery and Biological Evaluations of Halogenated 2,4-Diphenyl Indeno[1,2-b]pyridinol Derivatives as Potent Topoisomerase IIα-Targeted Chemotherapeutic Agents for Breast Cancer.,  62  (17): [PMID:31398033] [10.1021/acs.jmedchem.9b00970]

Source

Source(1):

• Scientific Literature