2-(4-(2-fluorobenzyloxy)benzyl)-3-hydroxynaphthalene-1,4-dione

ID: ALA482525

Max Phase: Preclinical

Molecular Formula: C24H17FO4

Molecular Weight: 388.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(Cc2ccc(OCc3ccccc3F)cc2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C24H17FO4/c25-21-8-4-1-5-16(21)14-29-17-11-9-15(10-12-17)13-20-22(26)18-6-2-3-7-19(18)23(27)24(20)28/h1-12,28H,13-14H2

Standard InChI Key:  HUXVLJGHSSRDSZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    6.7404    0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7392   -0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4521   -0.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4501    0.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1683    0.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1720   -0.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8918   -0.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6125   -0.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6088    0.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8844    0.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8943   -1.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8795    1.8013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3282   -0.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3218    0.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0377    0.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0367   -0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7517   -0.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4657   -0.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4602    0.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7447    0.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1821   -0.6621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8947   -0.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6111   -0.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6126   -1.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3282   -1.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0417   -1.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0351   -0.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3189   -0.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8994   -1.8920    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  9 14  1  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
  4  1  1  0
 16 17  1  0
  5 10  1  0
 17 18  2  0
  6  7  1  0
 18 19  1  0
  7  8  1  0
 19 20  2  0
 20 15  1  0
  8  9  2  0
 18 21  1  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  1  0
  7 11  2  0
 23 24  2  0
 24 25  1  0
 10 12  2  0
 25 26  2  0
  2  3  1  0
 26 27  1  0
  8 13  1  0
 27 28  2  0
 28 23  1  0
  3  6  2  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA482525

   ---

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: 388.39

Molecular Weight (Monoisotopic): 388.1111

AlogP: 4.84

#Rotatable Bonds: 5

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.44

CX Basic pKa: ┄

CX LogP: 4.66

CX LogD: 2.70

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.22

References

1. Sundriyal S, Viswanad B, Bharathy E, Ramarao P, Chakraborti AK, Bharatam PV..  (2008)  New PPARgamma ligands based on 2-hydroxy-1,4-naphthoquinone: computer-aided design, synthesis, and receptor-binding studies.,  18  (11): [PMID:18482837] [10.1016/j.bmcl.2008.04.072]

Source

Source(1):

• Scientific Literature