Methyl 3',5'-dichloro-4'-(alpha-D-mannopyranosyloxy)-biphenyl-4-carboxylate

ID: ALA1802190

Chembl Id: CHEMBL1802190

PubChem CID: 49856161

Max Phase: Preclinical

Molecular Formula: C20H20Cl2O8

Molecular Weight: 459.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(-c2cc(Cl)c(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)c(Cl)c2)cc1

Standard InChI:  InChI=1S/C20H20Cl2O8/c1-28-19(27)10-4-2-9(3-5-10)11-6-12(21)18(13(22)7-11)30-20-17(26)16(25)15(24)14(8-23)29-20/h2-7,14-17,20,23-26H,8H2,1H3/t14-,15-,16+,17+,20-/m1/s1

Standard InChI Key:  LGMPJLJIHTWSMR-GFAJBQDWSA-N

Alternative Forms

1. Parent:

   

   ALA1802190

   Methyl 3',5'-dichloro-4'-(alpha-D-mannopyranosyloxy)-biphenyl-4-carboxylate

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: 459.28

Molecular Weight (Monoisotopic): 458.0535

AlogP: 1.63

#Rotatable Bonds: 5

Polar Surface Area: 125.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: 0.92

References

1. Klein T, Abgottspon D, Wittwer M, Rabbani S, Herold J, Jiang X, Kleeb S, Lüthi C, Scharenberg M, Bezençon J, Gubler E, Pang L, Smiesko M, Cutting B, Schwardt O, Ernst B..  (2010)  FimH antagonists for the oral treatment of urinary tract infections: from design and synthesis to in vitro and in vivo evaluation.,  53  (24): [PMID:21105658] [10.1021/jm101011y]

Source

Source(1):

• Scientific Literature