5-(4-(3-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino)isoquinolin-1(2H)-one

ID: ALA4082878

PubChem CID: 87733533

Max Phase: Preclinical

Molecular Formula: C22H22F4N2O3

Molecular Weight: 438.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(CC(O)(CNc1cccc2c(=O)[nH]ccc12)C(F)(F)F)c1cccc(F)c1O

Standard InChI:  InChI=1S/C22H22F4N2O3/c1-20(2,15-6-4-7-16(23)18(15)29)11-21(31,22(24,25)26)12-28-17-8-3-5-14-13(17)9-10-27-19(14)30/h3-10,28-29,31H,11-12H2,1-2H3,(H,27,30)

Standard InChI Key:  ZANAAVXGSNLYBQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.0612  -14.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9425  -15.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9414  -16.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494  -16.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3591  -16.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3562  -15.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476  -14.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6452  -13.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7716  -15.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8932  -14.7668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7048  -13.9390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9930  -13.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2959  -13.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4747  -13.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1809  -13.5437    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.7655  -13.5490    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4686  -13.1370    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4727  -15.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2347  -14.7839    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.4213  -15.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
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 20 21  1  0
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 25 27  1  0
 25 28  1  0
 12 29  1  0
  4 30  1  0
 21 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4082878

   5-[[4-(3-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-2H-isoquinolin-1-one

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: 438.42

Molecular Weight (Monoisotopic): 438.1567

AlogP: 4.45

#Rotatable Bonds: 6

Polar Surface Area: 85.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.08

CX Basic pKa: 2.83

CX LogP: 3.93

CX LogD: 3.92

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -0.67

References

1. Berger M, Rehwinkel H, Schmees N, Schäcke H, Edman K, Wissler L, Reichel A, Jaroch S..  (2017)  Discovery of new selective glucocorticoid receptor agonist leads.,  27  (3): [PMID:28043796] [10.1016/j.bmcl.2016.12.047]

Source

Source(1):

• Scientific Literature