(S)-2-amino-N-(2-(((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)ethyl)-N-methylpropanamide

ID: ALA5275884

Max Phase: Preclinical

Molecular Formula: C15H24N4O7

Molecular Weight: 372.38

Names and Identifiers

Canonical SMILES:  C[C@H](N)C(=O)N(C)CCOC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H24N4O7/c1-8(16)13(23)18(2)5-6-25-7-9-11(21)12(22)14(26-9)19-4-3-10(20)17-15(19)24/h3-4,8-9,11-12,14,21-22H,5-7,16H2,1-2H3,(H,17,20,24)/t8-,9+,11+,12+,14+/m0/s1

Standard InChI Key:  MASRBPGCBQGLTN-XKYXEJCGSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.7127   -0.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    0.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6673    0.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848    0.6107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956    0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7100    0.6051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7100    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244    1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8533    1.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.6050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244    0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244   -0.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9968   -0.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5843   -1.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010   -1.1960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5096   -0.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0929   -0.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8898   -0.4623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4731   -1.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596   -1.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2700   -0.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8533   -1.4154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4835   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033    0.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  1
  4  3  1  0
  4  5  1  0
  5  6  1  1
  7  6  1  0
  8  7  2  0
  9  8  1  0
  9 10  2  0
 11  9  1  0
 12 11  1  0
  6 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
  3 15  1  0
 15 16  1  6
 14 17  1  6
  1 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  1
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5275884

   ---

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: 372.38

Molecular Weight (Monoisotopic): 372.1645

AlogP: -3.02

#Rotatable Bonds: 7

Polar Surface Area: 160.11

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.70

CX Basic pKa: 8.36

CX LogP: -3.05

CX LogD: -3.90

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.37

Np Likeness Score: 0.35

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