cyclohexyl (2''R),(2''S)-3,3''-anhydro-2-deoxy-2-C-(2'',3''-dihydroxypropyl)-alpha-D-glucopyranoside

ID: ALA1088772

PubChem CID: 46885476

Max Phase: Preclinical

Molecular Formula: C15H26O6

Molecular Weight: 302.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@H](OC2CCCCC2)[C@@H]2CC(O)CO[C@H]2[C@@H]1O

Standard InChI:  InChI=1S/C15H26O6/c16-7-12-13(18)14-11(6-9(17)8-19-14)15(21-12)20-10-4-2-1-3-5-10/h9-18H,1-8H2/t9?,11-,12-,13-,14-,15+/m1/s1

Standard InChI Key:  MDSDVSGOSNVXAE-ZMPBYDAFSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.3035   -7.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035   -8.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296   -7.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0166   -7.3563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -7.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4464   -7.3626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4488   -6.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1655   -6.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1698   -5.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4574   -4.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7388   -5.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7328   -6.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296   -8.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0146   -9.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0082   -9.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7152  -10.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4304   -9.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4383   -9.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4577   -8.2090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2957   -9.4085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886   -9.0126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724   -7.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1422  -10.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  1
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 14  1  0
  1  4  1  0
  2 14  1  0
  3  6  1  6
 13  3  1  0
  6  7  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7  8  1  0
 13 19  1  1
 14 20  1  6
  3  4  1  0
  5 22  1  0
  2 21  1  6
 17 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1088772

   (4aR,5S,7R,8S,8aR)-5-cyclohexyloxy-7-(hydroxymethyl)-2,3,4,4a,5,7,8,8a-octahydropyrano[3,2-c]pyran-3,8-diol

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: 302.37

Molecular Weight (Monoisotopic): 302.1729

AlogP: 0.18

#Rotatable Bonds: 3

Polar Surface Area: 88.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.09

CX Basic pKa: ┄

CX LogP: 0.32

CX LogD: 0.32

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: 1.91

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