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

ID: ALA1090109

PubChem CID: 15813952

Max Phase: Preclinical

Molecular Formula: C14H25NO6

Molecular Weight: 303.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@@H](OC2CCCCC2)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H25NO6/c1-8(17)15-11-13(19)12(18)10(7-16)21-14(11)20-9-5-3-2-4-6-9/h9-14,16,18-19H,2-7H2,1H3,(H,15,17)/t10-,11-,12-,13-,14+/m1/s1

Standard InChI Key:  FDLAXPMYQUZWTM-KSTCHIGDSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -3.8833   -6.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -7.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1713   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4593   -7.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4593   -6.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1713   -5.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -7.5760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466   -8.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4617   -8.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0327   -8.8146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1713   -8.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5972   -7.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5990   -5.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3123   -6.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7436   -5.9271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7412   -5.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255   -4.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211   -3.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325   -3.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500   -3.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4561   -4.6915    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
 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
M  END

Alternative Forms

1. Parent:

   

   ALA1090109

   N-[(2S,3R,4R,5S,6R)-2-cyclohexyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-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: 303.36

Molecular Weight (Monoisotopic): 303.1682

AlogP: -0.72

#Rotatable Bonds: 4

Polar Surface Area: 108.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.43

CX Basic pKa: ┄

CX LogP: -0.78

CX LogD: -0.78

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: 1.49

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