N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyloxy)tetrahydro-2H-pyran-3-yl)acetamide

ID: ALA1093122

PubChem CID: 10452519

Max Phase: Preclinical

Molecular Formula: C14H25NO11

Molecular Weight: 383.35

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](O)[C@@H](O)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H25NO11/c1-3(17)15-5-7(19)6(18)4(2-16)25-14(5)26-13-11(23)9(21)8(20)10(22)12(13)24/h4-14,16,18-24H,2H2,1H3,(H,15,17)/t4-,5-,6-,7-,8-,9-,10+,11-,12-,13-,14-/m1/s1

Standard InChI Key:  MRKTUVZZZRUSQR-JPUVNKLSSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -3.7833    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7833   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3593   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3593    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713    0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454   -0.8552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466   -1.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9327   -2.0937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713   -1.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4972   -0.8552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4990    0.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2123    0.3791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6436    0.7937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    1.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    2.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    3.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460    2.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    2.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0686    1.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579    3.2763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    4.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1999    3.2577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094    1.6121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583    1.0375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  4  7  1  6
  5 15  1  6
  1  2  1  0
 15 16  1  0
 16 17  1  0
  7  8  1  0
  1  6  1  0
  8  9  1  0
  2  3  1  0
  8 10  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  3  4  1  0
 21 22  1  6
  3 11  1  1
 20 23  1  6
  4  5  1  0
 19 24  1  1
  2 12  1  6
 18 25  1  6
  5  6  1  0
 17 26  1  1
  1 13  1  1
 16 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1093122

   1D-myo-inositol 2-acetamido-2-deoxy-alpha-D-glucopyranoside

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: 383.35

Molecular Weight (Monoisotopic): 383.1428

AlogP: -5.87

#Rotatable Bonds: 4

Polar Surface Area: 209.40

Molecular Species: NEUTRAL

HBA: 11

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.92

CX Basic pKa: ┄

CX LogP: -5.84

CX LogD: -5.84

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.22

Np Likeness Score: 1.44

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