3,3,6,6-Tetramethyl-9-(1-methyl-1H-indol-3-yl)-3,4,6,7-tetrahydroacridine-1,8-(2H,5H,9H,10H)-dione

ID: ALA3121553

PubChem CID: 76336192

Max Phase: Preclinical

Molecular Formula: C26H30N2O2

Molecular Weight: 402.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(C2C3=C(CC(C)(C)CC3=O)NC3=C2C(=O)CC(C)(C)C3)c2ccccc21

Standard InChI:  InChI=1S/C26H30N2O2/c1-25(2)10-17-23(20(29)12-25)22(16-14-28(5)19-9-7-6-8-15(16)19)24-18(27-17)11-26(3,4)13-21(24)30/h6-9,14,22,27H,10-13H2,1-5H3

Standard InChI Key:  NONIOTXDBASBHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   21.0620  -11.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4711  -12.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8870  -11.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7834  -11.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9584  -11.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3719  -12.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7834  -11.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0629  -11.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3399  -12.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4954  -12.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4954  -10.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2074  -11.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2039  -11.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9126  -12.3466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9197  -10.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6329  -11.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6291  -11.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3476  -10.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3502   -9.8767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4954   -9.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9220   -9.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5920   -9.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3429   -8.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2571   -9.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5136   -8.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9654   -7.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1606   -8.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9070   -8.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4569   -9.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8302   -7.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  5  4  1  0
  4  6  1  0
  7  4  1  0
  7 11  1  0
  4 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 12 15  1  0
 13 14  1  0
 14 17  1  0
 16 15  1  0
 16 17  2  0
 16 18  1  0
 17  9  1  0
  9  1  1  0
  8 18  1  0
 18 19  2  0
 11 20  2  0
 15 21  1  0
 21 22  2  0
 22 23  1  0
 24 21  1  0
 25 23  1  0
  1  8  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 23 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3121553

   3,3,6,6-Tetramethyl-9-(1-methylindol-3-yl)-2,4,5,7,9,10-hexahydroacridine-1,8-dione

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: 402.54

Molecular Weight (Monoisotopic): 402.2307

AlogP: 5.15

#Rotatable Bonds: 1

Polar Surface Area: 51.10

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.72

Np Likeness Score: -0.51

References

1. Gündüz MG, Işli F, El-Khouly A, Yıldırım S, Öztürk Fincan GS, Şimşek R, Şafak C, Sarıoğlu Y, Öztürk Yıldırım S, Butcher RJ..  (2014)  Microwave-assisted synthesis and myorelaxant activity of 9-indolyl-1,8-acridinedione derivatives.,  75  [PMID:24534541] [10.1016/j.ejmech.2014.01.059]

Source

Source(1):

• Scientific Literature