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

ID: ALA3121719

Chembl Id: CHEMBL3121719

PubChem CID: 76325368

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](OCC(COc2ccc3ccccc3c2)Oc2ccc3ccccc3c2)[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)35-17-24(36-23-12-10-19-6-2-4-8-21(19)14-23)16-34-22-11-9-18-5-1-3-7-20(18)13-22/h1-14,24-33H,15-17H2/t24?,25-,26-,27+,28+,29+/m1/s1

Standard InChI Key:  NBDTZUYTNXHJOL-MJYFDKBTSA-N

Alternative Forms

1. Parent:

   

   ALA3121719

   (2S,3S,4S,5S,6R)-2-(2,3-dinaphthalen-2-yloxypropoxy)-6-(hydroxymethyl)oxane-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: 0.64

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