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

ID: ALA5291255

Max Phase: Preclinical

Molecular Formula: C16H16N2O8

Molecular Weight: 364.31

Names and Identifiers

Canonical SMILES:  O=C(OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H]1O)c1ccccc1O

Standard InChI:  InChI=1S/C16H16N2O8/c19-9-4-2-1-3-8(9)15(23)25-7-10-12(21)13(22)14(26-10)18-6-5-11(20)17-16(18)24/h1-6,10,12-14,19,21-22H,7H2,(H,17,20,24)/t10-,12-,13-,14-/m1/s1

Standard InChI Key:  OGLDYJNJUMJAPU-FMKGYKFTSA-N

Molfile:  

 
     RDKit          2D

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    3.6038    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006    0.9832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0203    1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099    0.3426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5933   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -0.0272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3798   -1.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1190    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    0.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -0.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243   -1.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5464    0.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735    0.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    1.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366   -0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6299   -1.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621   -0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4006    0.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087    0.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2223   -1.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  5  4  1  0
  5  6  1  0
  6  7  1  0
  7  1  1  0
  6  8  2  0
  9  5  1  1
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  9 14  1  0
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 21 19  2  0
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 23 22  2  0
 24 23  1  0
 25 24  2  0
 19 25  1  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5291255

   ---

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: 364.31

Molecular Weight (Monoisotopic): 364.0907

AlogP: -1.28

#Rotatable Bonds: 4

Polar Surface Area: 151.08

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.41

CX Basic pKa: ┄

CX LogP: 0.43

CX LogD: 0.42

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.49

Np Likeness Score: 0.91

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