ID: ALA1917476

Max Phase: Preclinical

Molecular Formula: C14H17N3O5

Molecular Weight: 307.31

Molecule Type: Small molecule

Representations

Canonical SMILES:  OC[C@H]1O[C@H](n2cc(-c3ccccc3)nn2)[C@@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H17N3O5/c18-7-10-11(19)12(20)13(21)14(22-10)17-6-9(15-16-17)8-4-2-1-3-5-8/h1-6,10-14,18-21H,7H2/t10-,11-,12+,13+,14+/m1/s1

Standard InChI Key:  SLCZDPXCZLKLKY-DGTMBMJNSA-N

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

Properties

Molecular Weight: 307.31

Molecular Weight (Monoisotopic): 307.1168

AlogP: -1.08

#Rotatable Bonds: 3

Polar Surface Area: 120.86

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.33

CX Basic pKa:

CX LogP: -0.36

CX LogD: -0.36

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: 0.23

References

1. Schwardt O, Rabbani S, Hartmann M, Abgottspon D, Wittwer M, Kleeb S, Zalewski A, Smieško M, Cutting B, Ernst B..  (2011)  Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.,  19  (21): [PMID:21962988] [10.1016/j.bmc.2011.08.057]

2. Mydock-McGrane L, Cusumano Z, Han Z, Binkley J, Kostakioti M, Hannan T, Pinkner JS, Klein R, Kalas V, Crowley J, Rath NP, Hultgren SJ, Janetka JW..  (2016)  Antivirulence C-Mannosides as Antibiotic-Sparing, Oral Therapeutics for Urinary Tract Infections.,  59  (20): [PMID:27689912] [10.1021/acs.jmedchem.6b00948]

3. Tomašič T, Rabbani S, Jakob RP, Reisner A, Jakopin Ž, Maier T, Ernst B, Anderluh M..  (2021)  Does targeting Arg98 of FimH lead to high affinity antagonists?,  211  [PMID:33340913] [10.1016/j.ejmech.2020.113093]

Source

Source(1):

• Scientific Literature