3,6-Dimethyl-9-(2-chloro-3-trifluoromethylphenyl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione

ID: ALA2263268

PubChem CID: 76308585

Max Phase: Preclinical

Molecular Formula: C22H21ClF3NO2

Molecular Weight: 423.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1CC(=O)C2=C(C1)NC1=C(C(=O)CC(C)C1)C2c1cccc(C(F)(F)F)c1Cl

Standard InChI:  InChI=1S/C22H21ClF3NO2/c1-10-6-14-19(16(28)8-10)18(20-15(27-14)7-11(2)9-17(20)29)12-4-3-5-13(21(12)23)22(24,25)26/h3-5,10-11,18,27H,6-9H2,1-2H3

Standard InChI Key:  NURUYHHKVUOICL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.6910   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910   -4.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -5.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -3.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1015   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026   -4.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -5.1476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8048   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5136   -3.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5139   -4.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157   -5.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9216   -4.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9214   -3.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2151   -3.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137   -2.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -2.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289   -5.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838   -5.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8038   -2.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5120   -2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5102   -1.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8008   -1.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0919   -1.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0972   -2.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3003   -2.0827    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3749   -1.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630   -1.4900    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698   -0.2481    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604   -0.6605    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  4 16  2  0
 12 17  1  0
  2 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  8 19  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2263268

   9-[2-Chloro-3-(trifluoromethyl)phenyl]-3,6-dimethyl-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: 423.86

Molecular Weight (Monoisotopic): 423.1213

AlogP: 5.55

#Rotatable Bonds: 1

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.46

CX LogD: 4.46

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: -0.57

References

1. Gozde Gunduz M, Evrim Dogan A, Simsek R, Erol K, Safak C.  (2009)  Substituted 9-aryl-1,8-acridinedione derivatives and their effects on potassium channels,  18  (4): [10.1007/s00044-008-9129-9]

Source

Source(1):

• Scientific Literature