1,3-Bis(1H-pyrrole-2-carboxamido)propan-2-yl alpha-D-mannopyranoside

ID: ALA3121705

Chembl Id: CHEMBL3121705

PubChem CID: 76321751

Max Phase: Preclinical

Molecular Formula: C19H26N4O8

Molecular Weight: 438.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCC(CNC(=O)c1ccc[nH]1)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)c1ccc[nH]1

Standard InChI:  InChI=1S/C19H26N4O8/c24-9-13-14(25)15(26)16(27)19(31-13)30-10(7-22-17(28)11-3-1-5-20-11)8-23-18(29)12-4-2-6-21-12/h1-6,10,13-16,19-21,24-27H,7-9H2,(H,22,28)(H,23,29)/t13-,14-,15+,16+,19+/m1/s1

Standard InChI Key:  JTLKDODEDOJWDU-CLLBMXBRSA-N

Alternative Forms

1. Parent:

   

   ALA3121705

   N-[3-(1H-pyrrole-2-carbonylamino)-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl]-1H-pyrrole-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: 438.44

Molecular Weight (Monoisotopic): 438.1751

AlogP: -2.31

#Rotatable Bonds: 9

Polar Surface Area: 189.16

Molecular Species: NEUTRAL

HBA: 8

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: -2.48

CX LogD: -2.48

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.21

Np Likeness Score: 0.83

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