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

ID: ALA4451277

Chembl Id: CHEMBL4451277

PubChem CID: 71768870

Max Phase: Preclinical

Molecular Formula: C16H21NO5

Molecular Weight: 307.35

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H21NO5/c1-10-14(19)16(21)15(20)12(22-10)9-17-13(18)8-7-11-5-3-2-4-6-11/h2-8,10,12,14-16,19-21H,9H2,1H3,(H,17,18)/b8-7+/t10-,12+,14+,15+,16+/m0/s1

Standard InChI Key:  NJLORPYFUUWZNP-NPLZYVICSA-N

Alternative Forms

1. Parent:

   

   ALA4451277

   (E)-3-phenyl-N-[[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-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: 307.35

Molecular Weight (Monoisotopic): 307.1420

AlogP: -0.31

#Rotatable Bonds: 4

Polar Surface Area: 99.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.63

CX Basic pKa: ┄

CX LogP: -0.08

CX LogD: -0.08

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: 0.91

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