2-Phenylbenzo[h]quinoline-4-carboxylic acid

ID: ALA3627925

Cas Number: 5278-87-5

PubChem CID: 270179

Max Phase: Preclinical

Molecular Formula: C20H13NO2

Molecular Weight: 299.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2ccccc2)nc2c1ccc1ccccc12

Standard InChI:  InChI=1S/C20H13NO2/c22-20(23)17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H,(H,22,23)

Standard InChI Key:  DULGCYHBYNNEPB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    1.7503   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332    0.6928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    2.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7151    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0346    0.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3115    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2683    2.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9482    3.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6713    2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -3.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1105   -4.4061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1887   -4.3905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0
  9  4  2  0
  3  2  2  0
  2  1  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  6 15  1  0
 21 22  1  0
 21 23  2  0
  8 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3627925

   2-Phenylbenzo[h]quinoline-4-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: 299.33

Molecular Weight (Monoisotopic): 299.0946

AlogP: 4.75

#Rotatable Bonds: 2

Polar Surface Area: 50.19

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.56

CX Basic pKa: 0.34

CX LogP: 4.81

CX LogD: 1.45

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: -0.66

References

1. Russo CM, Adhikari AA, Wallach DR, Fernandes S, Balch AN, Kerr WG, Chisholm JD..  (2015)  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5'-phosphatase (SHIP).,  25  (22): [PMID:26453006] [10.1016/j.bmcl.2015.09.034]

Source

Source(1):

• Scientific Literature