N-benzyl-1-((2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(methylthio)-tetrahydro-2H-pyran-4-yl)-1H-1,2,3-triazole-4-carboxamide

ID: ALA500137

Chembl Id: CHEMBL500137

PubChem CID: 11675582

Max Phase: Preclinical

Molecular Formula: C17H22N4O5S

Molecular Weight: 394.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS[C@@H]1O[C@H](CO)[C@H](O)[C@H](n2cc(C(=O)NCc3ccccc3)nn2)[C@H]1O

Standard InChI:  InChI=1S/C17H22N4O5S/c1-27-17-15(24)13(14(23)12(9-22)26-17)21-8-11(19-20-21)16(25)18-7-10-5-3-2-4-6-10/h2-6,8,12-15,17,22-24H,7,9H2,1H3,(H,18,25)/t12-,13+,14+,15-,17+/m1/s1

Standard InChI Key:  XOPJQNRJGIFUQS-HNLJFRNMSA-N

Alternative Forms

1. Parent:

   

   ALA500137

   N-benzyl-1-((2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(methylthio)-tetrahydro-2H-pyran-4-yl)-1H-1,2,3-triazole-4-carboxamide

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: 394.45

Molecular Weight (Monoisotopic): 394.1311

AlogP: -0.45

#Rotatable Bonds: 6

Polar Surface Area: 129.73

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.61

CX Basic pKa: ┄

CX LogP: 0.15

CX LogD: 0.15

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.66

References

1. Giguère D, Bonin MA, Cloutier P, Patnam R, St-Pierre C, Sato S, Roy R..  (2008)  Synthesis of stable and selective inhibitors of human galectins-1 and -3.,  16  (16): [PMID:18674915] [10.1016/j.bmc.2008.06.044]

2. Salameh BA, Cumpstey I, Sundin A, Leffler H, Nilsson UJ..  (2010)  1H-1,2,3-triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors.,  18  (14): [PMID:20538469] [10.1016/j.bmc.2010.05.040]

3. Rajput VK, Leffler H, Nilsson UJ, Mukhopadhyay B..  (2014)  Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists.,  24  (15): [PMID:24973029] [10.1016/j.bmcl.2014.05.063]

Source

Source(1):

• Scientific Literature