4-(4-(1-ethyl-2-propyl-1H-imidazol-5-yl)pyrimidin-2-ylamino)-N-(2-methoxyethyl)benzenesulfonamide

ID: ALA4090176

PubChem CID: 10310396

Max Phase: Preclinical

Molecular Formula: C21H28N6O3S

Molecular Weight: 444.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1ncc(-c2ccnc(Nc3ccc(S(=O)(=O)NCCOC)cc3)n2)n1CC

Standard InChI:  InChI=1S/C21H28N6O3S/c1-4-6-20-23-15-19(27(20)5-2)18-11-12-22-21(26-18)25-16-7-9-17(10-8-16)31(28,29)24-13-14-30-3/h7-12,15,24H,4-6,13-14H2,1-3H3,(H,22,25,26)

Standard InChI Key:  WFEFIZVUPISKQK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.5168  -16.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0277  -15.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2088  -15.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7239  -15.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9800  -14.3441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7643  -14.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9344  -13.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3133  -13.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3133  -13.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0264  -12.6232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4568   -9.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7395   -8.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7395   -8.0860    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   17.1700   -6.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1700   -5.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8832   -5.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5254   -7.2905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9420   -7.8724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0264   -9.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0264  -10.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3132  -11.3874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5960  -11.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5960  -12.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6465  -14.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8986  -15.1284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  5  1  0
  8  9  1  0
  9 10  2  0
 11 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 15 14  1  0
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 19 20  1  0
 20 21  1  0
 21 22  1  0
 17 23  2  0
 17 24  2  0
 25 16  1  0
 26 25  2  0
 13 26  1  0
 27 11  2  0
 28 27  1  0
 29 28  2  0
  9 29  1  0
 30  8  2  0
 31 30  1  0
  4 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090176

   4-[[4-(3-ethyl-2-propylimidazol-4-yl)pyrimidin-2-yl]amino]-N-(2-methoxyethyl)benzenesulfonamide

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: 444.56

Molecular Weight (Monoisotopic): 444.1944

AlogP: 2.98

#Rotatable Bonds: 11

Polar Surface Area: 111.03

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.61

CX Basic pKa: 5.89

CX LogP: 2.63

CX LogD: 2.62

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -1.73

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(1):

• Scientific Literature