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

ID: ALA3590173

Chembl Id: CHEMBL3590173

PubChem CID: 71768902

Max Phase: Preclinical

Molecular Formula: C16H21NO6

Molecular Weight: 323.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](CNC(=O)/C=C/c2ccccc2)[C@@H](O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H21NO6/c1-22-16-15(21)14(20)13(19)11(23-16)9-17-12(18)8-7-10-5-3-2-4-6-10/h2-8,11,13-16,19-21H,9H2,1H3,(H,17,18)/b8-7+/t11-,13-,14+,15+,16+/m1/s1

Standard InChI Key:  LHFOPICMJLPBDI-DAGKTCNCSA-N

Alternative Forms

1. Parent:

   

   ALA3590173

   (E)-3-phenyl-N-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]prop-2-enamide

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: 323.35

Molecular Weight (Monoisotopic): 323.1369

AlogP: -0.73

#Rotatable Bonds: 5

Polar Surface Area: 108.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.22

CX Basic pKa: ┄

CX LogP: -0.22

CX LogD: -0.22

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.53

Np Likeness Score: 0.95

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