(1s,4s)-4-(6-amino-2-chloro-9H-purin-9-yl)-N-(4-(trifluoromethylsulfonyl)phenyl)cyclohexanecarboxamide

ID: ALA5091650

PubChem CID: 134214624

Max Phase: Preclinical

Molecular Formula: C19H18ClF3N6O3S

Molecular Weight: 502.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(Cl)nc2c1ncn2[C@H]1CC[C@@H](C(=O)Nc2ccc(S(=O)(=O)C(F)(F)F)cc2)CC1

Standard InChI:  InChI=1S/C19H18ClF3N6O3S/c20-18-27-15(24)14-16(28-18)29(9-25-14)12-5-1-10(2-6-12)17(30)26-11-3-7-13(8-4-11)33(31,32)19(21,22)23/h3-4,7-10,12H,1-2,5-6H2,(H,26,30)(H2,24,27,28)/t10-,12+

Standard InChI Key:  IWCNLFJSRUUYDE-KLPPZKSPSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   25.0891  -13.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3060  -14.3897    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.8908  -13.8016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8430  -13.7127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5600  -13.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.8412  -12.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1277  -13.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1289  -12.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3447  -12.2185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8588  -12.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3427  -13.5532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8374  -11.2329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0865  -14.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2795  -14.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0224  -15.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5709  -15.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3802  -15.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6407  -14.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3117  -16.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5033  -16.8527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9541  -16.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8609  -17.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2162  -15.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6679  -14.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8584  -15.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6004  -15.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1505  -16.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5888  -14.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5814  -15.6239    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.8774  -14.3792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.8716  -15.2069    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.2756  -13.7108    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  7 13  1  0
 14 12  1  1
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  1
 20 21  1  0
 21 22  1  0
 20 23  2  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
 26  2  1  0
  2 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
  5 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5091650

   ---

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: 502.91

Molecular Weight (Monoisotopic): 502.0802

AlogP: 3.73

#Rotatable Bonds: 4

Polar Surface Area: 132.86

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.04

CX Basic pKa: 2.03

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.52

Np Likeness Score: -1.33

References

1. Quartieri F, Nesi M, Avanzi NR, Borghi D, Casale E, Corti E, Cucchi U, Donati D, Fasolini M, Felder ER, Galvani A, Giorgini ML, Lomolino A, Menichincheri M, Orrenius C, Perrera C, Re Depaolini S, Riccardi-Sirtori F, Salsi E, Isacchi A, Gnocchi P..  (2021)  Identification of unprecedented ATP-competitive choline kinase inhibitors.,  51  [PMID:34416377] [10.1016/j.bmcl.2021.128310]

Source

Source(1):

• Scientific Literature