rac-2-(5-(3,5-Dichloro-4-((1-(2-fluorophenyl)ethyl)amino)quinolin-6-yl)pyrimidin-2-yl)propan-2-ol

ID: ALA4743794

PubChem CID: 126531748

Max Phase: Preclinical

Molecular Formula: C24H21Cl2FN4O

Molecular Weight: 471.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(Nc1c(Cl)cnc2ccc(-c3cnc(C(C)(C)O)nc3)c(Cl)c12)c1ccccc1F

Standard InChI:  InChI=1S/C24H21Cl2FN4O/c1-13(15-6-4-5-7-18(15)27)31-22-17(25)12-28-19-9-8-16(21(26)20(19)22)14-10-29-23(30-11-14)24(2,3)32/h4-13,32H,1-3H3,(H,28,31)

Standard InChI Key:  PSNVRMJOZNVVGO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    7.2928   -7.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0852   -7.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749   -6.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7932   -7.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7932   -6.2346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5023   -5.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2073   -6.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2073   -7.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5023   -7.4646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0395   -4.6003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486   -5.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486   -5.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0395   -6.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3346   -5.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6255   -6.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9164   -5.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9164   -5.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6255   -4.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3346   -5.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0395   -7.0560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486   -7.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4536   -7.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486   -8.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0395   -8.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0395   -9.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486   -9.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4536   -9.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4536   -8.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3346   -8.2818    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.6255   -7.0560    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.4536   -6.2346    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.0897   -8.2818    0.0000 O   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
 15 30  1  0
 12 31  1  0
  7 16  1  0
  2  4  1  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743794

   ---

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: 471.36

Molecular Weight (Monoisotopic): 470.1076

AlogP: 6.54

#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: 5.64

CX LogP: 5.33

CX LogD: 5.32

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -0.91

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