6-chloro-N-(1-(2-chloroacetyl)pyrrolidin-3-yl)-7-iodo-4-oxo-1,4-dihydroquinoline-2-carboxamide

ID: ALA5278066

Max Phase: Preclinical

Molecular Formula: C16H14Cl2IN3O3

Molecular Weight: 494.12

Names and Identifiers

Canonical SMILES:  O=C(NC1CCN(C(=O)CCl)C1)c1cc(=O)c2cc(Cl)c(I)cc2[nH]1

Standard InChI:  InChI=1S/C16H14Cl2IN3O3/c17-6-15(24)22-2-1-8(7-22)20-16(25)13-5-14(23)9-3-10(18)11(19)4-12(9)21-13/h3-5,8H,1-2,6-7H2,(H,20,25)(H,21,23)

Standard InChI Key:  UWXHPPZSMIHWRD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -3.8266    0.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1121    0.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002    0.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -0.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8266   -0.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -0.7416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709   -0.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2562   -0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583   -0.3291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709    0.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855    1.7338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2562   -1.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264   -0.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4783   -1.0191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659   -1.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2591   -1.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5413    0.9082    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5413   -0.7453    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035   -1.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161   -0.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161   -1.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413   -1.7338    0.0000 Cl  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
  1  6  1  0
  6  5  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  0
  3 12  1  0
 12 13  1  0
  8 13  2  0
 12 14  2  0
  9 15  2  0
 16 11  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 11  1  0
  1 20  1  0
  6 21  1  0
 17 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278066

   ---

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: 494.12

Molecular Weight (Monoisotopic): 492.9457

AlogP: 2.36

#Rotatable Bonds: 3

Polar Surface Area: 82.27

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.82

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -1.39

References

1. Cheng R, Lv X, Bu H, Xu Q, Wu J, Xie K, Tang J, Wang L, Zhuang J, Zhang Y, Zhang Y, Yan C, Lai Y..  (2022)  Design, synthesis, and evaluation of 4(1H)-quinolinone and urea derivatives as KRAS^G12C inhibitors with potent antitumor activity against KRAS-mutant non-small cell lung cancer.,  244  [PMID:36228411] [10.1016/j.ejmech.2022.114808]

Source

Source(1):

• Scientific Literature