8-Cyclopentyl-6-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)-3,4-dihydroisoquinolin-1(2H)-one

ID: ALA3235353

PubChem CID: 73437616

Max Phase: Preclinical

Molecular Formula: C25H30N2O2

Molecular Weight: 390.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn(-c2cc3c(c(C4CCCC4)c2)C(=O)NCC3)c2c1C(=O)CC(C)(C)C2

Standard InChI:  InChI=1S/C25H30N2O2/c1-15-14-27(20-12-25(2,3)13-21(28)22(15)20)18-10-17-8-9-26-24(29)23(17)19(11-18)16-6-4-5-7-16/h10-11,14,16H,4-9,12-13H2,1-3H3,(H,26,29)

Standard InChI Key:  AMWZXPSBURRZMG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.3958   -5.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6900   -6.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4003   -6.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9811   -3.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9800   -4.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6880   -4.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3977   -4.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6892   -5.2923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3501   -5.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0969   -6.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6401   -7.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4394   -6.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1465   -5.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3858   -7.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2822   -6.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0288   -5.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8037   -7.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6862   -2.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3979   -3.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1032   -2.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1029   -2.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3913   -1.6054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6799   -2.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9704   -1.6116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2733   -2.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1922   -2.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3928   -1.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9843   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5314   -3.1683    0.0000 C   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
  6  7  2  0
  7 19  1  0
 18  4  1  0
  8 16  1  0
 15 10  1  0
  9  8  1  0
  6  8  1  0
  9 10  2  0
  9 13  1  0
 10 11  1  0
 11 12  1  0
 12  2  1  0
  2 13  1  0
 11 14  2  0
 15 16  2  0
 15 17  1  0
 18 19  2  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
  4 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3235353

   8-Cyclopentyl-6-(3,6,6-Trimethyl-4-Oxo-4,5,6,7-Tetrahydro-1h-Indol-1-Yl)-3,4-Dihydroisoquinolin-1(2h)-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: 390.53

Molecular Weight (Monoisotopic): 390.2307

AlogP: 4.88

#Rotatable Bonds: 2

Polar Surface Area: 51.10

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.89

CX LogD: 4.89

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.79

Np Likeness Score: 0.15

References

1. Ernst JT, Neubert T, Liu M, Sperry S, Zuccola H, Turnbull A, Fleck B, Kargo W, Woody L, Chiang P, Tran D, Chen W, Snyder P, Alcacio T, Nezami A, Reynolds J, Alvi K, Goulet L, Stamos D..  (2014)  Identification of novel HSP90α/β isoform selective inhibitors using structure-based drug design. demonstration of potential utility in treating CNS disorders such as Huntington's disease.,  57  (8): [PMID:24673104] [10.1021/jm500042s]

2. Mishra SJ,Liu W,Beebe K,Banerjee M,Kent CN,Munthali V,Koren J,Taylor JA,Neckers LM,Holzbeierlein J,Blagg BSJ.  (2021)  The Development of Hsp90β-Selective Inhibitors to Overcome Detriments Associated with pan-Hsp90 Inhibition.,  64  (3.0): [PMID:33428418] [10.1021/acs.jmedchem.0c01700]

Source

Source(1):

• Scientific Literature