1-(3-chloro-4-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)-1H-indole-5-carboxylic acid

ID: ALA2079375

Chembl Id: CHEMBL2079375

PubChem CID: 53251477

Max Phase: Preclinical

Molecular Formula: C21H20ClNO8

Molecular Weight: 449.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2c(ccn2-c2ccc(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)c(Cl)c2)c1

Standard InChI:  InChI=1S/C21H20ClNO8/c22-13-8-12(23-6-5-10-7-11(20(28)29)1-3-14(10)23)2-4-15(13)30-21-19(27)18(26)17(25)16(9-24)31-21/h1-8,16-19,21,24-27H,9H2,(H,28,29)/t16-,17-,18+,19+,21+/m1/s1

Standard InChI Key:  UPSQJAOEPOVWAK-AGRFSFNASA-N

Alternative Forms

1. Alternative Forms:

   

   ALA2079375

   sodium;1-[3-chloro-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]indole-5-carboxylate

2. Parent:

   

   ALA2079375

   1-[3-chloro-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]indole-5-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: 449.84

Molecular Weight (Monoisotopic): 449.0877

AlogP: 1.16

#Rotatable Bonds: 5

Polar Surface Area: 141.61

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.63

CX Basic pKa: ┄

CX LogP: 1.64

CX LogD: -1.69

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: 0.37

References

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

Source

Source(1):

• Scientific Literature