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

ID: ALA1222017

Chembl Id: CHEMBL1222017

Cas Number: 13319-32-9

PubChem CID: 444514

Max Phase: Preclinical

Molecular Formula: C24H41N3O16

Molecular Weight: 627.60

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H41N3O16/c1-7(31)25-13-18(36)20(11(5-29)39-22(13)38)42-24-15(27-9(3)33)19(37)21(12(6-30)41-24)43-23-14(26-8(2)32)17(35)16(34)10(4-28)40-23/h10-24,28-30,34-38H,4-6H2,1-3H3,(H,25,31)(H,26,32)(H,27,33)/t10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+,24+/m1/s1

Standard InChI Key:  WZZVUHWLNMNWLW-VFCSDQTKSA-N

Alternative Forms

1. Parent:

   

   ALA1222017

   TRIACETYLCHITOTRIOSE

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: 627.60

Molecular Weight (Monoisotopic): 627.2487

AlogP: -7.14

#Rotatable Bonds: 10

Polar Surface Area: 295.29

Molecular Species: NEUTRAL

HBA: 16

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.41

CX Basic pKa: ┄

CX LogP: -7.34

CX LogD: -7.34

Aromatic Rings: ┄

Heavy Atoms: 43

QED Weighted: 0.11

Np Likeness Score: 1.09

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