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

ID: ALA3121703

Chembl Id: CHEMBL3121703

PubChem CID: 76332597

Max Phase: Preclinical

Molecular Formula: C25H32N2O10

Molecular Weight: 520.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)NCC(CNC(=O)c2ccc(OC)cc2)O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)cc1

Standard InChI:  InChI=1S/C25H32N2O10/c1-34-16-7-3-14(4-8-16)23(32)26-11-18(12-27-24(33)15-5-9-17(35-2)10-6-15)36-25-22(31)21(30)20(29)19(13-28)37-25/h3-10,18-22,25,28-31H,11-13H2,1-2H3,(H,26,32)(H,27,33)/t19-,20-,21+,22+,25+/m1/s1

Standard InChI Key:  CMZMSEULXCKSFO-QBSOXGLUSA-N

Alternative Forms

1. Parent:

   

   ALA3121703

   4-methoxy-N-[3-[(4-methoxybenzoyl)amino]-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl]benzamide

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: 520.54

Molecular Weight (Monoisotopic): 520.2057

AlogP: -0.95

#Rotatable Bonds: 11

Polar Surface Area: 176.04

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: -0.79

CX LogD: -0.79

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.22

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