N-(4-cyanophenyl)-N-((1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methyl)methanesulfonamide

ID: ALA4083074

PubChem CID: 137646502

Max Phase: Preclinical

Molecular Formula: C17H21N5O7S

Molecular Weight: 439.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)N(Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1)c1ccc(C#N)cc1

Standard InChI:  InChI=1S/C17H21N5O7S/c1-30(27,28)22(12-4-2-10(6-18)3-5-12)8-11-7-21(20-19-11)17-16(26)15(25)14(24)13(9-23)29-17/h2-5,7,13-17,23-26H,8-9H2,1H3/t13-,14-,15+,16-,17-/m1/s1

Standard InChI Key:  ACIUXMSFECKXFG-NQNKBUKLSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   10.9916   -9.6291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5834  -10.3458    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4082  -10.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2817  -10.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0668  -10.3870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7358  -10.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4039  -10.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -9.6005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3251   -9.5994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1882  -10.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8021  -10.0904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6317   -9.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7567  -11.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6747  -10.0863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8926  -10.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7157  -11.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3274  -11.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1160  -11.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823   -9.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4580   -8.9758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298  -11.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520  -12.5044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7293  -11.9990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2469   -8.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0770   -7.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2919   -7.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6767   -8.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8498   -9.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1205   -6.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9490   -6.0606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  1
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  7 10  1  0
 10 11  1  0
 11  2  1  0
 11 12  1  0
  2 13  1  0
  4 14  1  0
  4 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 15 19  1  1
 19 20  1  0
 16 21  1  6
 17 22  1  1
 18 23  1  6
 12 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 12  1  0
 26 29  1  0
 29 30  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4083074

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 439.45

Molecular Weight (Monoisotopic): 439.1162

AlogP: -1.91

#Rotatable Bonds: 6

Polar Surface Area: 182.03

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.33

CX Basic pKa: ┄

CX LogP: -2.13

CX LogD: -2.13

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -0.76

References

1. Alaoui S, Dufies M, Driowya M, Demange L, Bougrin K, Robert G, Auberger P, Pagès G, Benhida R..  (2017)  Synthesis and anti-cancer activities of new sulfonamides 4-substituted-triazolyl nucleosides.,  27  (9): [PMID:28325600] [10.1016/j.bmcl.2017.03.018]

Source

Source(1):

• Scientific Literature