rac-4-((7-ethyl-5-methyl-8-(1-methyl-1H-pyrazol-3-yl)-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-N-(3-hydroxypropyl)benzenesulfonamide

ID: ALA4175615

PubChem CID: 145975475

Max Phase: Preclinical

Molecular Formula: C22H28N8O4S

Molecular Weight: 500.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC1C(=O)N(C)c2cnc(Nc3ccc(S(=O)(=O)NCCCO)cc3)nc2N1c1ccn(C)n1

Standard InChI:  InChI=1S/C22H28N8O4S/c1-4-17-21(32)29(3)18-14-23-22(26-20(18)30(17)19-10-12-28(2)27-19)25-15-6-8-16(9-7-15)35(33,34)24-11-5-13-31/h6-10,12,14,17,24,31H,4-5,11,13H2,1-3H3,(H,23,25,26)

Standard InChI Key:  KHBSTEQSSXYFCY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   38.1645  -19.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5772  -20.2606    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.9897  -19.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2898  -20.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2887  -21.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0008  -21.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7146  -21.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7118  -20.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9990  -20.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8661  -20.6695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4271  -21.9039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.1342  -21.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8433  -21.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8357  -20.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1279  -20.6708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.5532  -20.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   44.2609  -20.2595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.2627  -19.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6838  -20.2666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.6769  -21.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6728  -22.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2554  -22.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5919  -23.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8406  -23.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6578  -23.9758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.9141  -23.1999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.1349  -24.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1591  -20.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1605  -19.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4535  -19.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4550  -18.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4  2  1  0
  2 10  1  0
  7 11  1  0
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 12 13  2  0
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 16 14  1  0
 14 15  2  0
 15 12  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 19 24  1  0
 24 25  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 26  2  0
 18 26  1  0
 29 31  1  0
 10 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175615

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 500.59

Molecular Weight (Monoisotopic): 500.1954

AlogP: 1.51

#Rotatable Bonds: 9

Polar Surface Area: 145.58

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.63

CX Basic pKa: 2.85

CX LogP: 1.54

CX LogD: 1.54

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -1.37

References

1. Zhan MM, Yang Y, Luo J, Zhang XX, Xiao X, Li S, Cheng K, Xie Z, Tu Z, Liao C..  (2018)  Design, synthesis, and biological evaluation of novel highly selective polo-like kinase 2 inhibitors based on the tetrahydropteridin chemical scaffold.,  143  [PMID:29220793] [10.1016/j.ejmech.2017.11.058]

Source

Source(1):

• Scientific Literature