1,3-Diphenoxypropan-2-yl alpha-D-mannopyranoside

ID: ALA3121708

Chembl Id: CHEMBL3121708

PubChem CID: 76325365

Max Phase: Preclinical

Molecular Formula: C21H26O8

Molecular Weight: 406.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@H](OC(COc2ccccc2)COc2ccccc2)[C@@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C21H26O8/c22-11-17-18(23)19(24)20(25)21(29-17)28-16(12-26-14-7-3-1-4-8-14)13-27-15-9-5-2-6-10-15/h1-10,16-25H,11-13H2/t17-,18-,19+,20+,21+/m1/s1

Standard InChI Key:  BUKPHDMXJOXEGW-MJCUULBUSA-N

Alternative Forms

1. Parent:

   

   ALA3121708

   (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[2-phenoxy-1-(phenoxymethyl)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: 406.43

Molecular Weight (Monoisotopic): 406.1628

AlogP: 0.33

#Rotatable Bonds: 9

Polar Surface Area: 117.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 1.06

CX LogD: 1.06

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: 0.96

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