Acetic acid 2-acetoxy-1-(3,4,5-trihydroxy-6-sulfomethyl-tetrahydro-pyran-2-yloxymethyl)-ethyl ester

ID: ALA1159523

PubChem CID: 46905180

Max Phase: Preclinical

Molecular Formula: C13H22O12S

Molecular Weight: 402.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H22O12S/c1-6(14)22-3-8(24-7(2)15)4-23-13-12(18)11(17)10(16)9(25-13)5-26(19,20)21/h8-13,16-18H,3-5H2,1-2H3,(H,19,20,21)/t8?,9-,10-,11+,12-,13+/m1/s1

Standard InChI Key:  QYDUPKWHIDQOGZ-NSIFWNNTSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
    6.2243    5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    5.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7953    5.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7953    4.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2243    4.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9388    5.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9388    3.8304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    3.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809    3.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809    5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    5.0679    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6519    5.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    4.3534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830    4.4845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6532    5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3677    5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0822    5.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3677    6.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6532    6.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6532    7.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9388    7.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3677    7.9554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7967    5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5111    5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7967    6.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  6  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  6
  6  8  1  6
  5  9  1  1
  4 10  1  6
  3 11  1  1
 11 12  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 18 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1159523

   [(2S,3S,4S,5R,6S)-6-(2,3-diacetyloxypropoxy)-3,4,5-trihydroxyoxan-2-yl]methanesulfonic acid

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: 402.37

Molecular Weight (Monoisotopic): 402.0832

AlogP: -2.81

#Rotatable Bonds: 8

Polar Surface Area: 186.12

Molecular Species: ACID

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -1.22

CX Basic pKa: ┄

CX LogP: -3.02

CX LogD: -5.39

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.24

Np Likeness Score: 1.69

References

1. Kurihara H, Ando J, Hatano M, Kawabata J.  (1995)  Sulfoquinovosyldiacylglycerol as an -glucosidase inhibitor,  5  (12): [10.1016/0960-894X(95)00196-Z]

Source

Source(1):

• Scientific Literature