5'-O-[N-(D-alanyl)-sulfamoyl]adenosine

ID: ALA5283680

Max Phase: Preclinical

Molecular Formula: C14H21N7O7S

Molecular Weight: 431.43

Names and Identifiers

Canonical SMILES:  C[C@@H](N)C(=O)NS(=O)(=O)OC[C@H]1O[C@@H](Cn2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H21N7O7S/c1-6(15)14(24)20-29(25,26)27-3-8-11(23)10(22)7(28-8)2-21-5-19-9-12(16)17-4-18-13(9)21/h4-8,10-11,22-23H,2-3,15H2,1H3,(H,20,24)(H2,16,17,18)/t6-,7+,8-,10+,11-/m1/s1

Standard InChI Key:  JEDANUNJCYBTAT-MWRVJPDDSA-N

Molfile:  

 
     RDKit          2D

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   -0.5657   -0.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1878   -0.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9023   -0.3506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -0.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224   -0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    0.0533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0924    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    1.3882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3619    1.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3619    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0764   -0.1041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908    1.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0764    1.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0764    2.3708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798   -1.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593   -1.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1926   -2.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923   -2.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871   -0.5769    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -1.0620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4086   -0.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0762   -1.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4086    0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737    0.1390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3989    0.1390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7908   -0.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0762   -2.0367    0.0000 N   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
  6  7  1  0
  8  7  1  0
  8  9  2  0
  9 10  1  0
 11  7  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 10 15  1  0
 14 15  2  0
 15 16  1  0
  5 17  1  0
  3 18  1  0
 17 18  1  0
 18 19  1  6
 17 20  1  6
  1 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 21 26  2  0
 21 27  2  0
 24 28  1  6
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283680

   ---

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: 431.43

Molecular Weight (Monoisotopic): 431.1223

AlogP: -3.38

#Rotatable Bonds: 7

Polar Surface Area: 217.80

Molecular Species: ACID

HBA: 13

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.75

CX Basic pKa: 6.75

CX LogP: -4.15

CX LogD: -4.17

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: 0.20

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