6-[4-Hydroxy-3-(trifluoromethyl)phenyl]-1-naphthol

ID: ALA1917897

PubChem CID: 56643459

Max Phase: Preclinical

Molecular Formula: C17H11F3O2

Molecular Weight: 304.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(-c2ccc3c(O)cccc3c2)cc1C(F)(F)F

Standard InChI:  InChI=1S/C17H11F3O2/c18-17(19,20)14-9-11(5-7-16(14)22)10-4-6-13-12(8-10)2-1-3-15(13)21/h1-9,21-22H

Standard InChI Key:  RBRJVQYANZHRMU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -3.8598  -12.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8609  -13.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1461  -14.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1479  -12.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325  -12.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318  -13.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165  -14.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0014  -13.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0062  -12.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221  -12.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442  -14.9819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2973  -12.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4200  -12.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1315  -12.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269  -11.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4049  -11.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036  -11.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8383  -11.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8482  -12.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529  -13.7182    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5604  -12.4767    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5583  -13.3042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3 11  1  0
  2  3  1  0
  5  6  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  1  2  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  5  4  2  0
 15 18  1  0
  8  9  1  0
 14 19  1  0
  4  1  1  0
 19 20  1  0
  9 10  2  0
 19 21  1  0
 10  5  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1917897

   6-[4-Hydroxy-3-(trifluoromethyl)phenyl]naphthalen-1-ol

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: 304.27

Molecular Weight (Monoisotopic): 304.0711

AlogP: 4.94

#Rotatable Bonds: 1

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.22

CX Basic pKa: ┄

CX LogP: 4.88

CX LogD: 4.82

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.67

Np Likeness Score: 0.09

References

1. Wetzel M, Marchais-Oberwinkler S, Perspicace E, Möller G, Adamski J, Hartmann RW..  (2011)  Introduction of an electron withdrawing group on the hydroxyphenylnaphthol scaffold improves the potency of 17β-hydroxysteroid dehydrogenase type 2 (17β-HSD2) inhibitors.,  54  (21): [PMID:21972996] [10.1021/jm2008453]

Source

Source(1):

• Scientific Literature