5-((3aS,9bR)-6-ethoxy-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-4-yl)-1H-pyrrole-2-carboxylic acid

ID: ALA5191254

PubChem CID: 168287853

Max Phase: Preclinical

Molecular Formula: C19H20N2O3

Molecular Weight: 324.38

Names and Identifiers

Canonical SMILES:  CCOc1cccc2c1N[C@@H](c1ccc(C(=O)O)[nH]1)[C@H]1CC=C[C@@H]21

Standard InChI:  InChI=1S/C19H20N2O3/c1-2-24-16-8-4-7-13-11-5-3-6-12(11)17(21-18(13)16)14-9-10-15(20-14)19(22)23/h3-5,7-12,17,20-21H,2,6H2,1H3,(H,22,23)/t11-,12+,17-/m1/s1

Standard InChI Key:  YEXLLRYAYUEABM-BWACUDIHSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -3.0567    0.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    1.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6303    0.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6303    0.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -0.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0567    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -1.0651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257   -1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257   -2.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9156   -0.2407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010    0.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010    0.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9156    1.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7440    2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0766    2.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122    1.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991    1.9931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6242    0.9970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5136   -0.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2670    0.0946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066   -1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -1.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -0.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -1.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  3 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 12 16  1  0
 13 17  1  1
 12 18  1  1
 11 19  1  6
 20 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
 24 21  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5191254

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 324.38

Molecular Weight (Monoisotopic): 324.1474

AlogP: 3.94

#Rotatable Bonds: 4

Polar Surface Area: 74.35

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.71

CX Basic pKa: 2.90

CX LogP: 2.37

CX LogD: -0.58

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -0.31

References

1. Goebel GL, Hohnen L, Borgelt L, Hommen P, Qiu X, Lightfoot H, Wu P..  (2022)  Small molecules with tetrahydroquinoline-containing Povarov scaffolds as inhibitors disrupting the Protein-RNA interaction of LIN28-let-7.,  228  [PMID:34883291] [10.1016/j.ejmech.2021.114014]

Source

Source(1):

• Scientific Literature