(2R,3S,4R,5S)-3,4,5-triacetoxy-2-(acetoxymethyl)tetrahydropyran

ID: ALA489209

Cas Number: 13121-62-5

PubChem CID: 6710916

Max Phase: Preclinical

Molecular Formula: C14H20O9

Molecular Weight: 332.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1OC[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O

Standard InChI:  InChI=1S/C14H20O9/c1-7(15)19-5-11-13(22-9(3)17)14(23-10(4)18)12(6-20-11)21-8(2)16/h11-14H,5-6H2,1-4H3/t11-,12+,13+,14-/m1/s1

Standard InChI Key:  ULWHEXUWXLOVPV-ZOBORPQBSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.2448    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3275    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3275    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  1  7  1  6
  6  8  1  1
  5  9  1  1
  9 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  0
 18 19  1  0
 18 20  2  0
  8 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA489209

   [(2R,3S,4R,5S)-3,4,5-triacetyloxyoxan-2-yl]methyl acetate

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

Calculated Properties

Molecular Weight: 332.31

Molecular Weight (Monoisotopic): 332.1107

AlogP: -0.26

#Rotatable Bonds: 5

Polar Surface Area: 114.43

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.80

CX LogD: -0.80

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.50

Np Likeness Score: 1.52

References

1. Randhawa P, Farasati NA, Huang Y..  (2007)  BK Virus replication in vitro: limited effect of drugs interfering with viral uptake and intracellular transport.,  51  (12): [PMID:17893158] [10.1128/aac.00843-07]

Source

Source(1):

• Scientific Literature