(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-((N-(3-methoxyphenyl)methylsulfonamido)methyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

ID: ALA4100809

PubChem CID: 137660070

Max Phase: Preclinical

Molecular Formula: C25H32N4O12S

Molecular Weight: 612.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(N(Cc2cn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)nn2)S(C)(=O)=O)c1

Standard InChI:  InChI=1S/C25H32N4O12S/c1-14(30)37-13-21-22(38-15(2)31)23(39-16(3)32)24(40-17(4)33)25(41-21)28-11-18(26-27-28)12-29(42(6,34)35)19-8-7-9-20(10-19)36-5/h7-11,21-25H,12-13H2,1-6H3/t21-,22-,23+,24-,25-/m1/s1

Standard InChI Key:  TXWSGHYGRFWBGR-NHTNDUFYSA-N

Molfile:  

     RDKit          2D

 42 44  0  0  0  0  0  0  0  0999 V2000
   18.5921   -9.0460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1837   -9.7627    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0085   -9.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8821  -10.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6670   -9.8039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3362  -10.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0042   -9.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7504   -9.0173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9254   -9.0163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7885  -10.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4024   -9.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2320   -8.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3571  -10.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8472   -8.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6773   -7.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8923   -7.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2771   -7.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4501   -8.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2750   -9.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4928   -9.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3159  -10.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9276  -11.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7163  -10.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8826   -9.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0583   -8.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4480   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6238   -7.0314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6621   -8.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5300  -10.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9198  -10.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1338  -10.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0954   -9.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7523  -11.9214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9664  -12.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7910  -12.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3559  -11.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3296  -11.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1584  -12.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7718  -12.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3740  -12.4782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2914   -6.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1214   -5.9899    0.0000 C   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
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
  4 19  1  0
  4 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  1
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 21 29  1  6
 29 30  1  0
 30 31  1  0
 30 32  2  0
 22 33  1  1
 33 34  1  0
 34 35  1  0
 34 36  2  0
 23 37  1  6
 37 38  1  0
 38 39  1  0
 38 40  2  0
 15 41  1  0
 41 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100809

   ---

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: 612.61

Molecular Weight (Monoisotopic): 612.1737

AlogP: 0.51

#Rotatable Bonds: 11

Polar Surface Area: 191.75

Molecular Species: NEUTRAL

HBA: 15

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.38

CX LogD: -0.38

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.25

Np Likeness Score: -0.29

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