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

ID: ALA3121704

Chembl Id: CHEMBL3121704

PubChem CID: 76325364

Max Phase: Preclinical

Molecular Formula: C31H32N2O8

Molecular Weight: 560.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCC(CNC(=O)c1ccc2ccccc2c1)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)c1ccc2ccccc2c1

Standard InChI:  InChI=1S/C31H32N2O8/c34-17-25-26(35)27(36)28(37)31(41-25)40-24(15-32-29(38)22-11-9-18-5-1-3-7-20(18)13-22)16-33-30(39)23-12-10-19-6-2-4-8-21(19)14-23/h1-14,24-28,31,34-37H,15-17H2,(H,32,38)(H,33,39)/t25-,26-,27+,28+,31+/m1/s1

Standard InChI Key:  YZFOVACXPJIDOO-AGLBJMSUSA-N

Alternative Forms

1. Parent:

   

   ALA3121704

   N-[3-(naphthalene-2-carbonylamino)-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl]naphthalene-2-carboxamide

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: 560.60

Molecular Weight (Monoisotopic): 560.2159

AlogP: 1.34

#Rotatable Bonds: 9

Polar Surface Area: 157.58

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 1.50

CX LogD: 1.50

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.18

Np Likeness Score: 0.55

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