2,3-Bis(4-nitrophenoxy)propan-1-yl alpha-D-mannopyranoside

ID: ALA3121716

Chembl Id: CHEMBL3121716

PubChem CID: 76310830

Max Phase: Preclinical

Molecular Formula: C21H24N2O12

Molecular Weight: 496.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(OCC(CO[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)Oc2ccc([N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C21H24N2O12/c24-9-17-18(25)19(26)20(27)21(35-17)33-11-16(34-15-7-3-13(4-8-15)23(30)31)10-32-14-5-1-12(2-6-14)22(28)29/h1-8,16-21,24-27H,9-11H2/t16?,17-,18-,19+,20+,21+/m1/s1

Standard InChI Key:  IRJXJVDKIKUQRC-XZCODKSBSA-N

Alternative Forms

1. Parent:

   

   ALA3121716

   (2S,3S,4S,5S,6R)-2-[2,3-bis(4-nitrophenoxy)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: 496.43

Molecular Weight (Monoisotopic): 496.1329

AlogP: 0.15

#Rotatable Bonds: 11

Polar Surface Area: 204.12

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 0.94

CX LogD: 0.94

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.24

Np Likeness Score: 0.44

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