(S)-2-(5-(3-Chloro-4-((1-phenylethyl)amino)quinolin-6-yl)-pyrimidin-2-yl)propan-2-ol

ID: ALA4763268

PubChem CID: 162659132

Max Phase: Preclinical

Molecular Formula: C24H23ClN4O

Molecular Weight: 418.93

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](Nc1c(Cl)cnc2ccc(-c3cnc(C(C)(C)O)nc3)cc12)c1ccccc1

Standard InChI:  InChI=1S/C24H23ClN4O/c1-15(16-7-5-4-6-8-16)29-22-19-11-17(9-10-21(19)26-14-20(22)25)18-12-27-23(28-13-18)24(2,3)30/h4-15,30H,1-3H3,(H,26,29)/t15-/m0/s1

Standard InChI Key:  WFACESJCRDGXRJ-HNNXBMFYSA-N

Molfile:  

 
     RDKit          2D

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    6.7274   -6.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5198   -6.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3095   -5.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2287   -6.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2287   -5.4608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9378   -5.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6469   -5.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6469   -6.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9378   -6.6907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4750   -3.8264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1841   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1841   -5.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4750   -5.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7700   -5.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0610   -5.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3519   -5.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3519   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0610   -3.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7700   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8932   -5.4608    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.4750   -6.2821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1841   -6.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1841   -7.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8932   -7.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8932   -8.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1841   -9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4750   -8.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4750   -7.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5251   -7.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8916   -6.2818    0.0000 C   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
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 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
 12 20  1  0
 22 23  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
 21 22  1  0
 13 21  1  0
  7 16  1  0
  2  4  1  0
  2 29  1  0
 22 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4763268

   ---

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: 418.93

Molecular Weight (Monoisotopic): 418.1560

AlogP: 5.75

#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: 13.36

CX Basic pKa: 6.20

CX LogP: 4.61

CX LogD: 4.59

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -0.84

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