1,4-Dideoxy-1,4-[(R)-(5-deoxy-1,3-O-(m-nitrophenylmethylene)-D-arabinito1-5-yl]episulfoniumylidene]-D-arabinitol Chloride

ID: ALA5290456

Max Phase: Preclinical

Molecular Formula: C17H25ClNO9S+

Molecular Weight: 418.44

Names and Identifiers

Canonical SMILES:  Cl.O=[N+]([O-])c1cccc(C2OC[C@@H](O)[C@@H]([C@H](O)C[S@+]3C[C@@H](O)[C@H](O)[C@H]3CO)O2)c1

Standard InChI:  InChI=1S/C17H24NO9S.ClH/c19-5-14-15(23)12(21)7-28(14)8-13(22)16-11(20)6-26-17(27-16)9-2-1-3-10(4-9)18(24)25;/h1-4,11-17,19-23H,5-8H2;1H/q+1;/t11-,12-,13-,14-,15+,16+,17?,28+;/m1./s1

Standard InChI Key:  DQSJXNADOYKHDV-UWLLEWQTSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    1.0864   -0.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892    0.0137    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592    0.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4243    1.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8192    1.7190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8093   -0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6345   -0.1787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968   -0.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268   -1.7190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5992   -0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    1.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    1.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436    1.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588    1.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436    0.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739   -0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890   -1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2041   -0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2041    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713   -0.3994    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9192    0.4266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9192    1.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6345    0.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892    0.8389    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  6
  6  7  1  0
  5  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  6
 10 12  1  0
  4 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 20 25  1  0
 13 26  1  6
 27 24  1  0
 27 28  1  0
 27 29  2  0
M  CHG  3   4   1  27   1  28  -1
M  END

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: 418.44

Molecular Weight (Monoisotopic): 418.1166

AlogP: -1.55

#Rotatable Bonds: 6

Polar Surface Area: 162.75

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: -2.54

CX LogD: -2.54

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.21

Np Likeness Score: 1.22

References

1. Lu L, Chen J, Tao W, Wang Z, Liu D, Zhou J, Wu X, Sun H, Li W, Tanabe G, Muraoka O, Zhao B, Wu L, Xie W..  (2023)  Design and Synthesis of Sulfonium Derivatives: A Novel Class of α-Glucosidase Inhibitors with Potent In Vivo Antihyperglycemic Activities.,  66  (5): [PMID:36812150] [10.1021/acs.jmedchem.2c01984]

Source

Source(1):

• Scientific Literature