5-(phenethylamino)pyrimido[4,5-c]quinoline-8-carboxylic acid

ID: ALA5279015

Max Phase: Preclinical

Molecular Formula: C20H16N4O2

Molecular Weight: 344.37

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2c(c1)nc(NCCc1ccccc1)c1ncncc12

Standard InChI:  InChI=1S/C20H16N4O2/c25-20(26)14-6-7-15-16-11-21-12-23-18(16)19(24-17(15)10-14)22-9-8-13-4-2-1-3-5-13/h1-7,10-12H,8-9H2,(H,22,24)(H,25,26)

Standard InChI Key:  RNIUZVHLSOCFGG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -2.5043    1.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2238    2.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2314    2.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073    2.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7951    2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4968    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7746   -0.4036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601   -0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484   -0.3847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741   -0.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821   -1.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -2.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7601   -2.0567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7591   -2.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0414   -3.2853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3303   -2.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1017   -2.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8155   -1.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8098   -0.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864   -0.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -0.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5100    0.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -0.7715    0.0000 O   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  5  1  0
  5  6  2  0
  1  6  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 13 14  1  0
 10 15  1  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 18 19  1  0
 19 14  2  0
 13 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 12 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279015

   ---

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: 344.37

Molecular Weight (Monoisotopic): 344.1273

AlogP: 3.53

#Rotatable Bonds: 5

Polar Surface Area: 88.00

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.62

CX Basic pKa: 1.59

CX LogP: 3.32

CX LogD: -0.02

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -0.81

References

1. Davis-Gilbert ZW, Krämer A, Dunford JE, Howell S, Senbabaoglu F, Wells CI, Bashore FM, Havener TM, Smith JL, Hossain MA, Oppermann U, Drewry DH, Axtman AD..  (2023)  Discovery of a Potent and Selective Naphthyridine-Based Chemical Probe for Casein Kinase 2.,  14  (4): [PMID:37077385] [10.1021/acsmedchemlett.2c00530]

Source

Source(1):

• Scientific Literature