Methyl 4'-chloro-3'-(alpha-D-mannopyranosyloxy)-biphenyl-4-carboxylate

ID: ALA1802194

Chembl Id: CHEMBL1802194

PubChem CID: 49856356

Max Phase: Preclinical

Molecular Formula: C20H21ClO8

Molecular Weight: 424.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(-c2ccc(Cl)c(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)c2)cc1

Standard InChI:  InChI=1S/C20H21ClO8/c1-27-19(26)11-4-2-10(3-5-11)12-6-7-13(21)14(8-12)28-20-18(25)17(24)16(23)15(9-22)29-20/h2-8,15-18,20,22-25H,9H2,1H3/t15-,16-,17+,18+,20+/m1/s1

Standard InChI Key:  WDDBPKRIAIETTE-JGLNRKDHSA-N

Alternative Forms

1. Parent:

   

   ALA1802194

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

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: 424.83

Molecular Weight (Monoisotopic): 424.0925

AlogP: 0.97

#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: 1.66

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: 0.86

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