3-(3,4-dimethoxyphenyl)-N-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydropyran-2-yl]methyl]prop-2-enamide

ID: ALA4450053

Chembl Id: CHEMBL4450053

PubChem CID: 71768903

Max Phase: Preclinical

Molecular Formula: C18H25NO8

Molecular Weight: 383.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)NC[C@H]2O[C@H](OC)[C@@H](O)[C@@H](O)[C@@H]2O)cc1OC

Standard InChI:  InChI=1S/C18H25NO8/c1-24-11-6-4-10(8-12(11)25-2)5-7-14(20)19-9-13-15(21)16(22)17(23)18(26-3)27-13/h4-8,13,15-18,21-23H,9H2,1-3H3,(H,19,20)/b7-5+/t13-,15-,16+,17+,18+/m1/s1

Standard InChI Key:  MSOXNRHEAAYSSF-UJMIPNDGSA-N

Alternative Forms

1. Parent:

   

   ALA4450053

   (E)-3-(3,4-dimethoxyphenyl)-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: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 383.40

Molecular Weight (Monoisotopic): 383.1580

AlogP: -0.71

#Rotatable Bonds: 7

Polar Surface Area: 126.71

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.22

CX Basic pKa: ┄

CX LogP: -0.53

CX LogD: -0.53

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: 0.86

References

1. 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]

2. Parrino B, Schillaci D, Carnevale I, Giovannetti E, Diana P, Cirrincione G, Cascioferro S..  (2019)  Synthetic small molecules as anti-biofilm agents in the struggle against antibiotic resistance.,  161  [PMID:30347328] [10.1016/j.ejmech.2018.10.036]

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