6-ethoxy-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid

ID: ALA5208779

Cas Number: 2679950-04-8

PubChem CID: 99948059

Max Phase: Preclinical

Molecular Formula: C15H17NO3

Molecular Weight: 259.31

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H17NO3/c1-2-19-12-8-4-7-10-9-5-3-6-11(9)14(15(17)18)16-13(10)12/h3-5,7-9,11,14,16H,2,6H2,1H3,(H,17,18)/t9-,11-,14+/m0/s1

Standard InChI Key:  GRFQAIBGNQTAEC-NURSFMCSSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -2.1425    0.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    1.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160    0.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160    0.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261   -0.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261   -1.0651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7115   -1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7115   -2.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -0.2407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    0.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    0.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    1.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1702    2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9908    2.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264    1.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848    1.9930    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384    0.9970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -0.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -1.0659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425    0.1717    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
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208779

   (3aR,4S,9bS)-6-ethoxy-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid

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: 259.31

Molecular Weight (Monoisotopic): 259.1208

AlogP: 2.62

#Rotatable Bonds: 3

Polar Surface Area: 58.56

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.14

CX Basic pKa: 1.59

CX LogP: 2.09

CX LogD: -0.99

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.82

Np Likeness Score: -0.07

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