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

ID: ALA1222113

Chembl Id: CHEMBL1222113

PubChem CID: 46237146

Max Phase: Preclinical

Molecular Formula: C39H60N4O21

Molecular Weight: 920.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H](OC[C@H]2O[C@H](OCc3ccccc3)[C@H](NC(C)=O)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3NC(C)=O)[C@@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C39H60N4O21/c1-15(47)40-24-31(54)28(51)20(10-44)59-36(24)58-14-23-34(63-38-25(41-16(2)48)32(55)29(52)21(11-45)60-38)35(64-39-26(42-17(3)49)33(56)30(53)22(12-46)61-39)27(43-18(4)50)37(62-23)57-13-19-8-6-5-7-9-19/h5-9,20-39,44-46,51-56H,10-14H2,1-4H3,(H,40,47)(H,41,48)(H,42,49)(H,43,50)/t20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37+,38+,39+/m1/s1

Standard InChI Key:  ORNMTIYAZUJGEU-PBLZDYCUSA-N

Alternative Forms

1. Parent:

   

   ALA1222113

   GlcNAc(b1-3)[GlcNAc(b1-4)][GlcNAc(b1-6)]GlcNAc(a)-O-Bn

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: 920.92

Molecular Weight (Monoisotopic): 920.3750

AlogP: -6.95

#Rotatable Bonds: 17

Polar Surface Area: 372.31

Molecular Species: NEUTRAL

HBA: 21

HBD: 13

#RO5 Violations: 3

HBA (Lipinski): 25

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.52

CX Basic pKa: ┄

CX LogP: -7.03

CX LogD: -7.03

Aromatic Rings: 1

Heavy Atoms: 64

QED Weighted: 0.07

Np Likeness Score: 0.58

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