1-[N-(3-Nitrobenzenesulfonyl)-N-(2-pivaloyloxyethyl)aminomethyl]-5-fluoro-1H,3H-pyrimidin-2,4-dione

ID: ALA521967

PubChem CID: 25141400

Max Phase: Preclinical

Molecular Formula: C18H21FN4O8S

Molecular Weight: 472.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)OCCN(Cn1cc(F)c(=O)[nH]c1=O)S(=O)(=O)c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C18H21FN4O8S/c1-18(2,3)16(25)31-8-7-22(11-21-10-14(19)15(24)20-17(21)26)32(29,30)13-6-4-5-12(9-13)23(27)28/h4-6,9-10H,7-8,11H2,1-3H3,(H,20,24,26)

Standard InChI Key:  QCYQKDURYATAFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.5740  -13.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8595  -12.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451  -13.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306  -12.7837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839  -13.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839  -14.0212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306  -14.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306  -15.2587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839  -15.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984  -15.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984  -14.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839  -16.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451  -14.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306  -11.9587    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944  -11.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306  -11.1337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8069  -11.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6319  -11.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444  -11.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6319  -12.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069  -12.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2885  -12.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0029  -13.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2885  -11.9587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174  -13.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4154  -12.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5904  -13.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444  -13.3876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6319  -14.1021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694  -13.3876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7128  -15.6712    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 14 16  2  0
  4  5  1  0
 14 17  2  0
  2  3  1  0
 15 18  2  0
  6 11  1  0
 18 19  1  0
  7  8  1  0
 19 20  2  0
  8  9  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
 22 15  1  0
 10 11  2  0
  1 23  1  0
  5  6  1  0
 23 24  1  0
  9 12  2  0
 23 25  2  0
  6  7  1  0
 24 26  1  0
  7 13  2  0
 24 27  1  0
  1  2  1  0
 24 28  1  0
  4 14  1  0
  3  4  1  0
 14 15  1  0
 29 30  2  0
 29 31  1  0
 21 29  1  0
 10 32  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA521967

   2-[(5-Fluoro-2,4-dioxopyrimidin-1-yl)methyl-(3-nitrophenyl)sulfonylamino]ethyl 2,2-dimethylpropanoate

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: 472.45

Molecular Weight (Monoisotopic): 472.1064

AlogP: 0.82

#Rotatable Bonds: 8

Polar Surface Area: 161.68

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.10

CX Basic pKa: ┄

CX LogP: 2.02

CX LogD: 1.95

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -1.66

References

1. Gawin R, De Clercq E, Naesens L, Koszytkowska-Stawińska M..  (2008)  Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure.,  16  (18): [PMID:18778942] [10.1016/j.bmc.2008.08.041]

Source

Source(1):

• Scientific Literature