rac-2-(5-(3-Chloro-8-fluoro-4-((1-(2-fluorophenyl)ethyl)amino)-quinolin-6-yl)pyrimidin-2-yl)propan-2-ol

ID: ALA4744981

PubChem CID: 126531676

Max Phase: Preclinical

Molecular Formula: C24H21ClF2N4O

Molecular Weight: 454.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(Nc1c(Cl)cnc2c(F)cc(-c3cnc(C(C)(C)O)nc3)cc12)c1ccccc1F

Standard InChI:  InChI=1S/C24H21ClF2N4O/c1-13(16-6-4-5-7-19(16)26)31-21-17-8-14(9-20(27)22(17)28-12-18(21)25)15-10-29-23(30-11-15)24(2,3)32/h4-13,32H,1-3H3,(H,28,31)

Standard InChI Key:  HPYYKZIZHQUEJJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    6.7026   -7.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4950   -7.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2847   -7.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2031   -7.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2031   -6.6061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9121   -6.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6171   -6.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6171   -7.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9121   -7.8360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4493   -4.9717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1584   -5.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1584   -6.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4493   -6.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7444   -6.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0353   -6.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3262   -6.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3262   -5.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0353   -4.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7444   -5.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4493   -7.4274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1584   -7.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8634   -7.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1584   -8.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4493   -9.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4493   -9.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1584  -10.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8634   -9.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8634   -9.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7444   -8.6532    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.8634   -6.6061    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4995   -8.6532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0353   -4.1545    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 10 19  1  0
 14 19  1  0
 21 22  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 23 28  2  0
 24 29  1  0
 21 23  1  0
 20 21  1  0
 13 20  1  0
 12 30  1  0
  7 16  1  0
  2  4  1  0
  2 31  1  0
 18 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4744981

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.91

Molecular Weight (Monoisotopic): 454.1372

AlogP: 6.02

#Rotatable Bonds: 5

Polar Surface Area: 70.93

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.35

CX Basic pKa: 3.58

CX LogP: 4.91

CX LogD: 4.91

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.08

References

1. Xiao HY,Li N,Duan JJ,Jiang B,Lu Z,Ngu K,Tino J,Kopcho LM,Lu H,Chen J,Tebben AJ,Sheriff S,Chang CY,Yanchunas J,Calambur D,Gao M,Shuster DJ,Susulic V,Xie JH,Guarino VR,Wu DR,Gregor KR,Goldstine CB,Hynes J,Macor JE,Salter-Cid L,Burke JR,Shaw PJ,Dhar TGM.  (2020)  Biologic-like In Vivo Efficacy with Small Molecule Inhibitors of TNFα Identified Using Scaffold Hopping and Structure-Based Drug Design Approaches.,  63  (23): [PMID:33261314] [10.1021/acs.jmedchem.0c01732]

Source

Source(1):

• Scientific Literature