2,3-Bis((7-methoxynaphthalen-2-yl)oxy)propan-1-yl alpha-D-mannopyranoside

ID: ALA3121718

Chembl Id: CHEMBL3121718

PubChem CID: 76325367

Max Phase: Preclinical

Molecular Formula: C31H34O10

Molecular Weight: 566.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2ccc(OCC(CO[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)Oc3ccc4ccc(OC)cc4c3)cc2c1

Standard InChI:  InChI=1S/C31H34O10/c1-36-22-7-3-18-5-9-24(13-20(18)11-22)38-16-26(17-39-31-30(35)29(34)28(33)27(15-32)41-31)40-25-10-6-19-4-8-23(37-2)12-21(19)14-25/h3-14,26-35H,15-17H2,1-2H3/t26?,27-,28-,29+,30+,31+/m1/s1

Standard InChI Key:  DZVFPCOZZJGLGC-JUKRTZSXSA-N

Alternative Forms

1. Parent:

   

   ALA3121718

   (2S,3S,4S,5S,6R)-2-[2,3-bis[(7-methoxynaphthalen-2-yl)oxy]propoxy]-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: 566.60

Molecular Weight (Monoisotopic): 566.2152

AlogP: 2.65

#Rotatable Bonds: 11

Polar Surface Area: 136.30

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 2.72

CX LogD: 2.72

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.21

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