[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl 4-amino-2-hydroxy-benzoate

ID: ALA5290576

Max Phase: Preclinical

Molecular Formula: C16H17N3O8

Molecular Weight: 379.33

Names and Identifiers

Canonical SMILES:  Nc1ccc(C(=O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)c(O)c1

Standard InChI:  InChI=1S/C16H17N3O8/c17-7-1-2-8(9(20)5-7)15(24)26-6-10-12(22)13(23)14(27-10)19-4-3-11(21)18-16(19)25/h1-5,10,12-14,20,22-23H,6,17H2,(H,18,21,25)/t10-,12-,13-,14-/m1/s1

Standard InChI Key:  NBJLBIIZUDOBFX-FMKGYKFTSA-N

Molfile:  

 
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    4.7385    0.9832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582    1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478    0.3426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7282   -0.0272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176   -1.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9136    0.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5135    0.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264   -0.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2498   -0.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6622   -1.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6356    0.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9406    1.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987   -0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2920   -1.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0243   -0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0628    0.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3708    0.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -1.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7385   -1.2184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  9  5  1  1
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 19 25  1  0
 21 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290576

   ---

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: 379.33

Molecular Weight (Monoisotopic): 379.1016

AlogP: -1.70

#Rotatable Bonds: 4

Polar Surface Area: 177.10

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.50

CX Basic pKa: 2.35

CX LogP: -0.40

CX LogD: -0.41

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.31

Np Likeness Score: 0.93

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