ID: ALA254346

Max Phase: Preclinical

Molecular Formula: C12H17N3O6

Molecular Weight: 299.28

Molecule Type: Small molecule

Representations

Synonyms (1): Gluco-Nagstatin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)N[C@H]1c2nc(CC(=O)O)cn2[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H17N3O6/c1-5(17)13-9-11(21)10(20)7(4-16)15-3-6(2-8(18)19)14-12(9)15/h3,7,9-11,16,20-21H,2,4H2,1H3,(H,13,17)(H,18,19)/t7-,9-,10-,11-/m1/s1

Standard InChI Key:  XPJWMTPRJTUTBX-QCNRFFRDSA-N

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

Properties

Molecular Weight: 299.28

Molecular Weight (Monoisotopic): 299.1117

AlogP: -2.04

#Rotatable Bonds: 4

Polar Surface Area: 144.91

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.51

CX Basic pKa: 5.16

CX LogP: -4.05

CX LogD: -5.94

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.43

Np Likeness Score: 0.50

References

1. Stubbs KA, Balcewich M, Mark BL, Vocadlo DJ..  (2007)  Small molecule inhibitors of a glycoside hydrolase attenuate inducible AmpC-mediated beta-lactam resistance.,  282  (29): [PMID:17439950] [10.1074/jbc.m700084200]

2. Yuzwa SA, Macauley MS, Heinonen JE, Shan X, Dennis RJ, He Y, Whitworth GE, Stubbs KA, McEachern EJ, Davies GJ, Vocadlo DJ..  (2008)  A potent mechanism-inspired O-GlcNAcase inhibitor that blocks phosphorylation of tau in vivo.,  4  (8): [PMID:18587388] [10.1038/nchembio.96]

Source

Source(1):

• Scientific Literature