(S)-1-((4aR,5S)-1-(4-methoxyphenyl)-4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazol-5-yl)-1-(thiophen-3-yl)ethanol

ID: ALA4871994

PubChem CID: 164624724

Max Phase: Preclinical

Molecular Formula: C25H28N2O2S

Molecular Weight: 420.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-n2ncc3c2C=C2CCC[C@H]([C@@](C)(O)c4ccsc4)[C@@]2(C)C3)cc1

Standard InChI:  InChI=1S/C25H28N2O2S/c1-24-14-17-15-26-27(20-7-9-21(29-3)10-8-20)22(17)13-18(24)5-4-6-23(24)25(2,28)19-11-12-30-16-19/h7-13,15-16,23,28H,4-6,14H2,1-3H3/t23-,24-,25-/m0/s1

Standard InChI Key:  HOBAQIGXJTWJIG-SDHOMARFSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   14.6069  -24.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4288  -24.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0214  -23.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4325  -26.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1459  -26.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1459  -25.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4325  -25.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7190  -26.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7215  -25.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0096  -25.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0086  -26.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2960  -26.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2948  -25.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5111  -25.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0305  -25.9223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5132  -26.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2640  -27.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4549  -27.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2020  -28.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7531  -28.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5645  -28.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8178  -27.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1462  -23.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2257  -24.8720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4996  -29.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8991  -24.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4541  -23.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0418  -22.8520    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.2322  -23.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0499  -30.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7215  -24.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  9  7  1  0
  8  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  9  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 11  8  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 16 17  1  0
  7  2  1  0
  2 23  1  0
  7 24  1  6
 20 25  1  0
 23 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 23  2  0
 25 30  1  0
  9 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4871994

   ---

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: 420.58

Molecular Weight (Monoisotopic): 420.1871

AlogP: 5.60

#Rotatable Bonds: 4

Polar Surface Area: 47.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.84

CX Basic pKa: 1.60

CX LogP: 5.02

CX LogD: 5.02

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.60

Np Likeness Score: -0.16

References

1. Kennedy BJ, Lato AM, Fisch AR, Burke SJ, Kirkland JK, Prevatte CW, Dunlap LE, Smith RT, Vogiatzis KD, Collier JJ, Campagna SR..  (2021)  Potent Anti-Inflammatory, Arylpyrazole-Based Glucocorticoid Receptor Agonists That Do Not Impair Insulin Secretion.,  12  (10.0): [PMID:34676039] [10.1021/acsmedchemlett.1c00379]

Source

Source(1):

• Scientific Literature