4'-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)biphenyl-4-carboxylic acid

ID: ALA1852236

Chembl Id: CHEMBL1852236

PubChem CID: 49856164

Max Phase: Preclinical

Molecular Formula: C19H20O8

Molecular Weight: 376.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(-c2ccc(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)cc2)cc1

Standard InChI:  InChI=1S/C19H20O8/c20-9-14-15(21)16(22)17(23)19(27-14)26-13-7-5-11(6-8-13)10-1-3-12(4-2-10)18(24)25/h1-8,14-17,19-23H,9H2,(H,24,25)/t14-,15-,16+,17+,19+/m1/s1

Standard InChI Key:  ZLNPXKSDQKJSIZ-GJGATLCTSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1852236

   sodium;4-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]benzoate

2. Parent:

   

   ALA1852236

   4'-(alpha-D-Mannopyranosyloxy)-biphenyl-4-carboxylic acid

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: 376.36

Molecular Weight (Monoisotopic): 376.1158

AlogP: 0.23

#Rotatable Bonds: 5

Polar Surface Area: 136.68

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.08

CX Basic pKa: ┄

CX LogP: 0.71

CX LogD: -2.41

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: 1.16

References

1. Scharenberg M, Schwardt O, Rabbani S, Ernst B..  (2012)  Target Selectivity of FimH Antagonists.,  55  (22): [PMID:23088608] [10.1021/jm3010338]

2. Kleeb S, Pang L, Mayer K, Eris D, Sigl A, Preston RC, Zihlmann P, Sharpe T, Jakob RP, Abgottspon D, Hutter AS, Scharenberg M, Jiang X, Navarra G, Rabbani S, Smiesko M, Lüdin N, Bezençon J, Schwardt O, Maier T, Ernst B..  (2015)  FimH antagonists: bioisosteres to improve the in vitro and in vivo PK/PD profile.,  58  (5): [PMID:25666045] [10.1021/jm501524q]

3. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data