Phenyl-2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside

ID: ALA1092731

Cas Number: 1228577-52-3

PubChem CID: 7573794

Max Phase: Preclinical

Molecular Formula: C14H19NO5S

Molecular Weight: 313.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1Sc1ccccc1

Standard InChI:  InChI=1S/C14H19NO5S/c1-8(17)15-11-13(19)12(18)10(7-16)20-14(11)21-9-5-3-2-4-6-9/h2-6,10-14,16,18-19H,7H2,1H3,(H,15,17)/t10-,11-,12-,13-,14-/m1/s1

Standard InChI Key:  FRBANKZKTRTKBB-DHGKCCLASA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    5.6667    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0907    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0907    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787    1.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8046   -0.3010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8034   -1.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0883   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5173   -1.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -1.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -0.3010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9510    1.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2377    0.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8064    1.3479    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8088    2.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5252    2.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5280    3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8142    3.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0961    3.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0969    2.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  3 11  1  1
  4  5  1  0
  2 12  1  6
  5  6  1  0
  1 13  1  1
 13 14  1  0
  4  7  1  6
  5 15  1  6
  1  2  1  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
  1  6  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  2  3  1  0
 19 20  1  0
  8 10  2  0
 20 21  2  0
 21 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092731

   N-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-yl)acetamide

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: 313.38

Molecular Weight (Monoisotopic): 313.0984

AlogP: -0.28

#Rotatable Bonds: 4

Polar Surface Area: 99.02

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.54

CX Basic pKa: ┄

CX LogP: -0.49

CX LogD: -0.49

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.61

Np Likeness Score: 0.58

References

1. Gammon DW, Steenkamp DJ, Mavumengwana V, Marakalala MJ, Mudzunga TT, Hunter R, Munyololo M..  (2010)  Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol.,  18  (7): [PMID:20304659] [10.1016/j.bmc.2010.02.049]

Source

Source(1):

• Scientific Literature