rac-5-((1S,2R)-6-fluoro-2,5-dihydroxy-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-ylamino)isoquinolin-1(2H)-one

ID: ALA4085241

PubChem CID: 137648477

Max Phase: Preclinical

Molecular Formula: C22H20F4N2O3

Molecular Weight: 436.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C[C@](O)(C(F)(F)F)[C@@H](Nc2cccc3c(=O)[nH]ccc23)c2ccc(F)c(O)c21

Standard InChI:  InChI=1S/C22H20F4N2O3/c1-20(2)10-21(31,22(24,25)26)18(13-6-7-14(23)17(29)16(13)20)28-15-5-3-4-12-11(15)8-9-27-19(12)30/h3-9,18,28-29,31H,10H2,1-2H3,(H,27,30)/t18-,21+/m0/s1

Standard InChI Key:  ZILACWFNZFWDAS-GHTZIAJQSA-N

Molfile:  

     RDKit          2D

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    6.4674  -20.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8760  -21.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7492  -19.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1576  -18.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3707  -24.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760  -24.8831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7813  -24.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7813  -23.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3714  -23.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760  -23.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3578  -22.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6525  -22.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6632  -23.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729  -22.0186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7658  -21.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0510  -20.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498  -19.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418  -19.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345  -19.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6397  -20.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3482  -21.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397  -18.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250  -19.5845    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634  -24.8879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8559  -20.9076    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2436  -19.6315    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8871  -20.0336    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  5  4  1  0
  6  5  1  0
 11  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 12  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 13 17  1  0
 18 17  1  1
 18  2  1  0
 18 20  1  0
  2 19  1  0
 19  5  1  0
  5 21  1  0
 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
 23 27  1  0
  7 28  2  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085241

   ---

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: 436.41

Molecular Weight (Monoisotopic): 436.1410

AlogP: 4.50

#Rotatable Bonds: 2

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: 8.95

CX Basic pKa: 1.54

CX LogP: 3.74

CX LogD: 3.73

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -0.08

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