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

ID: ALA4548572

Chembl Id: CHEMBL4548572

PubChem CID: 155549148

Max Phase: Preclinical

Molecular Formula: C18H25NO7

Molecular Weight: 367.40

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H25NO7/c1-10-16(21)18(23)17(22)14(26-10)9-19-15(20)7-5-11-4-6-12(24-2)13(8-11)25-3/h4-8,10,14,16-18,21-23H,9H2,1-3H3,(H,19,20)/b7-5+/t10-,14+,16+,17+,18+/m0/s1

Standard InChI Key:  QROABCURGVOZGA-ZTSYIJMHSA-N

Alternative Forms

1. Parent:

   

   ALA4548572

   ---

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: 367.40

Molecular Weight (Monoisotopic): 367.1631

AlogP: -0.30

#Rotatable Bonds: 6

Polar Surface Area: 117.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.63

CX Basic pKa: ┄

CX LogP: -0.40

CX LogD: -0.40

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: 0.84

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

Source

Source(1):

• Scientific Literature