11-cyclohexyl-6H-isoindolo[2,1-a]indole-3-carboxylic acid

ID: ALA217807

PubChem CID: 11695645

Max Phase: Preclinical

Molecular Formula: C22H21NO2

Molecular Weight: 331.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2c(C3CCCCC3)c3n(c2c1)Cc1ccccc1-3

Standard InChI:  InChI=1S/C22H21NO2/c24-22(25)15-10-11-18-19(12-15)23-13-16-8-4-5-9-17(16)21(23)20(18)14-6-2-1-3-7-14/h4-5,8-12,14H,1-3,6-7,13H2,(H,24,25)

Standard InChI Key:  HBGPABVOJDCWGZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   -3.4282  -10.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4294  -11.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7150  -11.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168  -10.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1450  -10.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452   -9.4076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8589  -10.6444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020  -10.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971  -11.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058  -11.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453  -12.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4951  -13.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376  -13.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305  -14.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1188  -13.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1390  -12.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2110  -10.3785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7238  -11.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7267   -9.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597   -9.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599  -10.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725  -11.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853  -10.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -9.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7680   -9.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  3  1  0
  3  9  2  0
  5  6  1  0
  5  7  2  0
  1  5  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 18  1  0
  8  9  1  0
  1  2  2  0
  8  4  2  0
 18 21  1  0
 20 19  1  0
 19 17  1  0
  4  1  1  0
  9 10  1  0
 20 21  2  0
 10 18  2  0
 21 22  1  0
 17  8  1  0
 22 23  2  0
 23 24  1  0
 10 11  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA217807

   11-cyclohexyl-6H-isoindolo[2,1-a]indole-3-carboxylic acid

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: 331.42

Molecular Weight (Monoisotopic): 331.1572

AlogP: 5.42

#Rotatable Bonds: 2

Polar Surface Area: 42.23

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.62

CX Basic pKa: ┄

CX LogP: 5.39

CX LogD: 2.05

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -0.05

References

1. Ikegashira K, Oka T, Hirashima S, Noji S, Yamanaka H, Hara Y, Adachi T, Tsuruha J, Doi S, Hase Y, Noguchi T, Ando I, Ogura N, Ikeda S, Hashimoto H..  (2006)  Discovery of conformationally constrained tetracyclic compounds as potent hepatitis C virus NS5B RNA polymerase inhibitors.,  49  (24): [PMID:17125247] [10.1021/jm0610245]

Source

Source(1):

• Scientific Literature