(2R,3S,5R)-5-((((2R,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-3-yl hydrogen sulfate

ID: ALA5276580

Max Phase: Preclinical

Molecular Formula: C14H19F2N3O11S

Molecular Weight: 475.38

Names and Identifiers

Canonical SMILES:  NC[C@H]1O[C@@H](OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](OS(=O)(=O)O)C2(F)F)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H19F2N3O11S/c15-14(16)6(4-27-12-9(22)8(21)5(3-17)28-12)29-11(10(14)30-31(24,25)26)19-2-1-7(20)18-13(19)23/h1-2,5-6,8-12,21-22H,3-4,17H2,(H,18,20,23)(H,24,25,26)/t5-,6-,8-,9-,10+,11-,12-/m1/s1

Standard InChI Key:  VPBVJMCJBBKVAP-UMEAPJPCSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    3.0426   -0.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0426    0.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281    0.9720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136    0.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357   -0.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191   -0.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8055   -1.6261    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3889   -2.2095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -1.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2215   -2.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6148   -0.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2853    0.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9027    0.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5115    0.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0949    0.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918    0.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715    1.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0913    0.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4752   -0.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -1.1058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9351   -0.3298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6747    1.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4716    1.2474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1010   -0.7386    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6148   -1.1504    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281    1.7970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0426    2.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7571    1.7970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7571    0.9719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4716    2.2095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  6
  6  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  2  0
  5 11  1  0
 12 11  1  0
 13 12  1  0
 13  4  1  0
 12 14  1  1
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 19 18  1  0
 20 19  1  0
 20 16  1  0
 20 21  1  6
 19 22  1  6
 18 23  1  1
 23 24  1  0
 11 25  1  0
 11 26  1  0
 27  3  1  0
 28 27  2  0
 29 28  1  0
 30 29  1  0
  2 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5276580

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 475.38

Molecular Weight (Monoisotopic): 475.0708

AlogP: -3.32

#Rotatable Bonds: 7

Polar Surface Area: 212.63

Molecular Species: ZWITTERION

HBA: 12

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -2.23

CX Basic pKa: 8.76

CX LogP: -3.29

CX LogD: -3.30

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.25

Np Likeness Score: 1.38

References

1. Serpi M, Ferrari V, Pertusati F..  (2016)  Nucleoside Derived Antibiotics to Fight Microbial Drug Resistance: New Utilities for an Established Class of Drugs?,  59  (23): [PMID:27607900] [10.1021/acs.jmedchem.6b00325]

Source

Source(1):

• Scientific Literature