2,4,6-trimethyl-N-(((2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl)benzenesulfonamide

ID: ALA3590172

Chembl Id: CHEMBL3590172

PubChem CID: 71760917

Max Phase: Preclinical

Molecular Formula: C16H25NO7S

Molecular Weight: 375.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](CNS(=O)(=O)c2c(C)cc(C)cc2C)[C@@H](O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H25NO7S/c1-8-5-9(2)15(10(3)6-8)25(21,22)17-7-11-12(18)13(19)14(20)16(23-4)24-11/h5-6,11-14,16-20H,7H2,1-4H3/t11-,12-,13+,14+,16+/m1/s1

Standard InChI Key:  RVGBPVTVQRZPOK-NJURLYQPSA-N

Alternative Forms

1. Parent:

   

   ALA3590172

   2,4,6-trimethyl-N-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]benzenesulfonamide

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: 375.44

Molecular Weight (Monoisotopic): 375.1352

AlogP: -0.66

#Rotatable Bonds: 5

Polar Surface Area: 125.32

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.80

CX Basic pKa: ┄

CX LogP: 0.57

CX LogD: 0.57

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: 0.20

References

1. Pera NP, Pieters RJ.  (2014)  Towards bacterial adhesion-based therapeutics and detection methods,  5  (8): [10.1039/C3MD00346A]

2. Sommer R, Rox K, Wagner S, Hauck D, Henrikus SS, Newsad S, Arnold T, Ryckmans T, Brönstrup M, Imberty A, Varrot A, Hartmann RW, Titz A..  (2019)  Anti-biofilm Agents against Pseudomonas aeruginosa: A Structure-Activity Relationship Study of C-Glycosidic LecB Inhibitors.,  62  (20): [PMID:31553873] [10.1021/acs.jmedchem.9b01120]

3. Singh K, Kulkarni SS..  (2022)  Small Carbohydrate Derivatives as Potent Antibiofilm Agents.,  65  (13.0): [PMID:35777073] [10.1021/acs.jmedchem.1c01039]

4. Wagner S, Sommer R, Hinsberger S, Lu C, Hartmann RW, Empting M, Titz A..  (2016)  Novel Strategies for the Treatment of Pseudomonas aeruginosa Infections.,  59  (13): [PMID:26804741] [10.1021/acs.jmedchem.5b01698]

Source

Source(1):

• Scientific Literature