(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-((N-butylmethylsulfonamido)methyl)-1H-1,2,3-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate

ID: ALA4068912

PubChem CID: 137633510

Max Phase: Preclinical

Molecular Formula: C19H30N4O9S

Molecular Weight: 490.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN(Cc1cn([C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)nn1)S(C)(=O)=O

Standard InChI:  InChI=1S/C19H30N4O9S/c1-6-7-8-22(33(5,27)28)9-15-10-23(21-20-15)19-18(31-14(4)26)17(30-13(3)25)16(32-19)11-29-12(2)24/h10,16-19H,6-9,11H2,1-5H3/t16-,17-,18-,19-/m1/s1

Standard InChI Key:  OUJIYPLOPOSPKT-NCXUSEDFSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   15.3582   -4.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9499   -5.6291    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7747   -5.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5666   -6.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3916   -6.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6483   -5.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9791   -5.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3140   -5.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4333   -5.6703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8756   -7.3764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0808   -7.3751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5293   -5.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165   -6.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1317   -5.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188   -6.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9598   -5.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4153   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9295   -8.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2357   -8.2165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6963   -7.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1804   -7.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0327   -6.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1023   -6.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7705   -5.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5166   -4.8838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6917   -4.8828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5548   -5.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1686   -5.3736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9982   -4.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1232   -6.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2140   -4.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0435   -3.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2592   -3.2472    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  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  6  9  1  1
  5 10  1  6
  4 11  1  6
  8 12  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 11 17  1  0
 17 18  1  0
 17 19  2  0
 10 20  1  0
 20 21  1  0
 20 22  2  0
  9 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  9  1  0
 24 27  1  0
 27 28  1  0
 28  2  1  0
 28 29  1  0
  2 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4068912

   ---

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: 490.54

Molecular Weight (Monoisotopic): 490.1733

AlogP: 0.16

#Rotatable Bonds: 11

Polar Surface Area: 156.22

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.37

CX LogD: -0.37

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -0.19

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