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

ID: ALA3121706

Chembl Id: CHEMBL3121706

PubChem CID: 76332598

Max Phase: Preclinical

Molecular Formula: C25H32N2O8

Molecular Weight: 488.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccccc1)NCC(CNC(=O)Cc1ccccc1)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C25H32N2O8/c28-15-19-22(31)23(32)24(33)25(35-19)34-18(13-26-20(29)11-16-7-3-1-4-8-16)14-27-21(30)12-17-9-5-2-6-10-17/h1-10,18-19,22-25,28,31-33H,11-15H2,(H,26,29)(H,27,30)/t19-,22-,23+,24+,25+/m1/s1

Standard InChI Key:  SIQNVRXFBDMFNJ-CPSSSWKVSA-N

Alternative Forms

1. Parent:

   

   ALA3121706

   2-phenyl-N-[3-[(2-phenylacetyl)amino]-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl]acetamide

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: 488.54

Molecular Weight (Monoisotopic): 488.2159

AlogP: -1.11

#Rotatable Bonds: 11

Polar Surface Area: 157.58

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: -0.52

CX LogD: -0.52

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.23

Np Likeness Score: 0.67

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