N-((2R,3R,4R,5R,6R)-5-((2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

ID: ALA1222104

Chembl Id: CHEMBL1222104

PubChem CID: 46238071

Max Phase: Preclinical

Molecular Formula: C16H28N2O11

Molecular Weight: 424.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H28N2O11/c1-5(21)17-9-13(25)14(8(4-20)27-15(9)26)29-16-10(18-6(2)22)12(24)11(23)7(3-19)28-16/h7-16,19-20,23-26H,3-4H2,1-2H3,(H,17,21)(H,18,22)/t7-,8-,9-,10-,11+,12-,13-,14+,15?,16+/m1/s1

Standard InChI Key:  CDOJPCSDOXYJJF-FBDLHECSSA-N

Alternative Forms

1. Parent:

   

   ALA1222104

   GalNAc(b1-4)GalNAc

Molecule Features

Natural Product: Yes

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: 424.40

Molecular Weight (Monoisotopic): 424.1693

AlogP: -5.11

#Rotatable Bonds: 6

Polar Surface Area: 207.27

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.50

CX Basic pKa: ┄

CX LogP: -5.28

CX LogD: -5.28

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.20

Np Likeness Score: 1.62

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

Source(1):

• Scientific Literature