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

ID: ALA3121551

PubChem CID: 76336191

Max Phase: Preclinical

Molecular Formula: C22H22N2O2

Molecular Weight: 346.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(C2C3=C(CCCC3=O)NC3=C2C(=O)CCC3)c2ccccc21

Standard InChI:  InChI=1S/C22H22N2O2/c1-24-12-14(13-6-2-3-9-17(13)24)20-21-15(7-4-10-18(21)25)23-16-8-5-11-19(26)22(16)20/h2-3,6,9,12,20,23H,4-5,7-8,10-11H2,1H3

Standard InChI Key:  GTGHTIOCKHDIMD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
    1.3252  -10.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6053  -10.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822  -11.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3252  -11.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372  -11.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372   -9.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494  -10.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7458  -11.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4547  -11.4939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4617   -9.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1752  -10.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1713  -11.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8898   -9.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8925   -9.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372   -9.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641   -9.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1342   -8.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8851   -7.7541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044  -11.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7992   -8.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -7.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5074   -7.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025   -7.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -8.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9989   -8.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724   -7.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  1  6  1  0
  4  5  1  0
  5  8  1  0
  7  6  1  0
  7  8  2  0
  7 10  1  0
  8  9  1  0
  9 12  1  0
 11 10  1  0
 11 12  2  0
 11 13  1  0
 12  3  1  0
  3 19  1  0
  2 13  1  0
 13 14  2  0
  6 15  2  0
 10 16  1  0
 16 17  2  0
 17 18  1  0
 20 16  1  0
 21 18  1  0
 19  2  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
 18 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3121551

   9-(1-Methylindol-3-yl)-2,3,4,5,6,7,9,10-octahydroacridine-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: 346.43

Molecular Weight (Monoisotopic): 346.1681

AlogP: 3.88

#Rotatable Bonds: 1

Polar Surface Area: 51.10

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.73

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: -0.66

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