2-(acridin-9-ylmethyleneamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

ID: ALA4458806

PubChem CID: 155526638

Max Phase: Preclinical

Molecular Formula: C22H15N3S

Molecular Weight: 353.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(/N=C/c2c3ccccc3nc3ccccc23)sc2c1CCC2

Standard InChI:  InChI=1S/C22H15N3S/c23-12-17-16-8-5-11-21(16)26-22(17)24-13-18-14-6-1-3-9-19(14)25-20-10-4-2-7-15(18)20/h1-4,6-7,9-10,13H,5,8,11H2/b24-13+

Standard InChI Key:  AXYQGCIVQBOXBW-ZMOGYAJESA-N

Molfile:  

 
     RDKit          2D

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   37.2234   -8.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3966   -8.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9829   -8.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3947   -9.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6345   -8.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2218   -9.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6314  -10.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4525   -8.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.8644   -9.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4528  -10.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8637  -11.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6860  -11.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0958  -10.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6826   -9.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2182  -11.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6333  -11.8331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2201  -12.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3977  -12.6417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.5594  -13.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9447  -13.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2273  -13.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6179  -14.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9584  -14.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7783  -14.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3701  -13.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1807  -13.6524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  1  1  0
  5  6  1  0
  6  7  2  0
  7 10  1  0
  9  8  1  0
  8  5  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14  9  2  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 21  1  0
 20 19  1  0
 19 17  2  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 19 25  1  0
 25 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4458806

   ---

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: 353.45

Molecular Weight (Monoisotopic): 353.0987

AlogP: 5.56

#Rotatable Bonds: 2

Polar Surface Area: 49.04

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.68

CX LogP: 6.32

CX LogD: 6.32

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.35

Np Likeness Score: -1.43

References

1. Prasher P, Sharma M..  (2018)  Medicinal chemistry of acridine and its analogues.,  9  (10): [PMID:30429967] [10.1039/C8MD00384J]

2. Duvauchelle V, Meffre P, Benfodda Z..  (2022)  Recent contribution of medicinally active 2-aminothiophenes: A privileged scaffold for drug discovery.,  238  [PMID:35696863] [10.1016/j.ejmech.2022.114502]

Source

Source(1):

• Scientific Literature