(2R,3S,4R,5R)-2-ethoxy-3,4,5-trihydroxyhexane-1,6-diyl bis(dihydrogen phosphate)

ID: ALA2017786

PubChem CID: 70681219

Max Phase: Preclinical

Molecular Formula: C8H20O12P2

Molecular Weight: 370.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCO[C@H](COP(=O)(O)O)[C@@H](O)[C@H](O)[C@H](O)COP(=O)(O)O

Standard InChI:  InChI=1S/C8H20O12P2/c1-2-18-6(4-20-22(15,16)17)8(11)7(10)5(9)3-19-21(12,13)14/h5-11H,2-4H2,1H3,(H2,12,13,14)(H2,15,16,17)/t5-,6-,7-,8-/m1/s1

Standard InChI Key:  AUJSYRIHPYQIJY-WCTZXXKLSA-N

Molfile:  

     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
    7.3307    0.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0462    1.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6152    1.1699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7618    0.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0462    1.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7618   -0.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4731    1.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1887    0.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4731    1.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1887   -0.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9042    1.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6198    0.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8996    0.7592    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.3298    1.1782    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.3200    2.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0503    0.7761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0434    1.5973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1893    1.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8976   -0.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1858    0.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9001   -0.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9001   -1.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  6
 11 12  1  0
  1  2  1  0
  3 13  1  0
  4  7  1  0
 12 14  1  0
  2  4  1  0
 14 15  2  0
  7  8  1  0
 14 16  1  0
 14 17  1  0
  7  9  1  6
 13 18  2  0
  2  5  1  1
 13 19  1  0
  8 10  1  1
 13 20  1  0
  1  3  1  0
 10 21  1  0
  8 11  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2017786

   [(2R,3S,4R,5R)-2-ethoxy-3,4,5-trihydroxy-6-phosphonooxyhexyl] dihydrogen phosphate

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: 370.18

Molecular Weight (Monoisotopic): 370.0430

AlogP: -2.31

#Rotatable Bonds: 11

Polar Surface Area: 203.44

Molecular Species: ACID

HBA: 8

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.04

CX Basic pKa: ┄

CX LogP: -2.98

CX LogD: -9.80

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.19

Np Likeness Score: 0.95

References

1. Mabiala-Bassiloua CG, Arthus-Cartier G, Hannaert V, Thérisod H, Sygusch J, Thérisod M..  (2011)  Mannitol Bis-phosphate Based Inhibitors of Fructose 1,6-Bisphosphate Aldolases.,  2  (11): [PMID:24900268] [10.1021/ml200129s]

Source

Source(1):

• Scientific Literature