1,3-Bis(naphthalen-1-yloxy)propan-2-yl alpha-D-mannopyranoside

ID: ALA3121711

Chembl Id: CHEMBL3121711

PubChem CID: 76310828

Max Phase: Preclinical

Molecular Formula: C29H30O8

Molecular Weight: 506.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@H](OC(COc2cccc3ccccc23)COc2cccc3ccccc23)[C@@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C29H30O8/c30-15-25-26(31)27(32)28(33)29(37-25)36-20(16-34-23-13-5-9-18-7-1-3-11-21(18)23)17-35-24-14-6-10-19-8-2-4-12-22(19)24/h1-14,20,25-33H,15-17H2/t25-,26-,27+,28+,29+/m1/s1

Standard InChI Key:  DHDUJZRDNNTZBZ-PNHLWVRCSA-N

Alternative Forms

1. Parent:

   

   ALA3121711

   (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[2-(1-naphthyloxy)-1-(1-naphthyloxymethyl)ethoxy]tetrahydropyran-3,4,5-triol

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: 506.55

Molecular Weight (Monoisotopic): 506.1941

AlogP: 2.64

#Rotatable Bonds: 9

Polar Surface Area: 117.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 3.04

CX LogD: 3.04

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.27

Np Likeness Score: 0.74

References

1. Tomašić T, Hajšek D, Švajger U, Luzar J, Obermajer N, Petit-Haertlein I, Fieschi F, Anderluh M..  (2014)  Monovalent mannose-based DC-SIGN antagonists: targeting the hydrophobic groove of the receptor.,  75  [PMID:24556146] [10.1016/j.ejmech.2014.01.047]

2. Tomasic T, Rabbani S, Gobec M, Rascan IM, Podlipnik C, Ernst B, Anderluh M.  (2014)  Branched -d-mannopyranosides: a new class of potent FimH antagonists,  5  (8): [10.1039/C4MD00093E]

Source

Source(1):

• Scientific Literature