N,N'-(2S,2'R,3R,3'R,4R,4'R,5S,5'S,6R,6'R)-2,2'-((2R,3S,4R,5R,6R)-5-acetamido-2-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)methyl)-6-hydroxytetrahydro-2H-pyran-3,4-diyl)bis(oxy)bis(4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3,2-diyl)diacetamide

ID: ALA1222111

Chembl Id: CHEMBL1222111

PubChem CID: 49864585

Max Phase: Preclinical

Molecular Formula: C32H54N4O21

Molecular Weight: 830.79

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H]1[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)O[C@H]1O

Standard InChI:  InChI=1S/C32H54N4O21/c1-9(40)33-17-24(47)21(44)13(5-37)53-30(17)51-8-16-27(56-31-18(34-10(2)41)25(48)22(45)14(6-38)54-31)28(20(29(50)52-16)36-12(4)43)57-32-19(35-11(3)42)26(49)23(46)15(7-39)55-32/h13-32,37-39,44-50H,5-8H2,1-4H3,(H,33,40)(H,34,41)(H,35,42)(H,36,43)/t13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31+,32+/m1/s1

Standard InChI Key:  NPDPTVOAXHIGFY-XHVHYUDBSA-N

Alternative Forms

Associated Targets(Human)

CD69 Tchem Early activation antigen CD69 (107 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Klrb1a Killer cell lectin-like receptor subfamily B member 1A (24 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 830.79Molecular Weight (Monoisotopic): 830.3281AlogP: -9.17#Rotatable Bonds: 14
Polar Surface Area: 383.31Molecular Species: NEUTRALHBA: 21HBD: 14
#RO5 Violations: 3HBA (Lipinski): 25HBD (Lipinski): 14#RO5 Violations (Lipinski): 3
CX Acidic pKa: 11.30CX Basic pKa: CX LogP: -9.40CX LogD: -9.40
Aromatic Rings: Heavy Atoms: 57QED Weighted: 0.08Np Likeness Score: 0.82

References

1. Kovalová A, Ledvina M, Saman D, Zyka D, Kubícková M, Zídek L, Sklenár V, Pompach P, Kavan D, Bílý J, Vanek O, Kubínková Z, Libigerová M, Ivanová L, Antolíková M, Mrázek H, Rozbeský D, Hofbauerová K, Kren V, Bezouska K..  (2010)  Synthetic N-acetyl-D-glucosamine based fully branched tetrasaccharide, a mimetic of the endogenous ligand for CD69, activates CD69+ killer lymphocytes upon dimerization via a hydrophilic flexible linker.,  53  (10): [PMID:20433142] [10.1021/jm100055b]

Source