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

ID: ALA2017789

PubChem CID: 70689614

Max Phase: Preclinical

Molecular Formula: C8H20O12P2

Molecular Weight: 370.18

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  XQKKGWTUWPWHKT-OOJXKGFFSA-N

Molfile:  

     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.6219    0.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9064    0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    0.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909    0.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9064    1.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909   -0.2821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4795    0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317    0.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4795    1.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -0.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9516    0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    0.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0530    0.5434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.3772    0.9625    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.3672    1.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977    0.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0908    1.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7633    0.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551   -0.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7668    0.1369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090   -0.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8048   -0.8588    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
  8 21  1  0
  8 11  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2017789

   [(2R,3S,4R,5R)-2-ethyl-2,3,4,5-tetrahydroxy-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: -2.57

#Rotatable Bonds: 10

Polar Surface Area: 214.44

Molecular Species: ACID

HBA: 8

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.25

CX Basic pKa: ┄

CX LogP: -3.17

CX LogD: -9.66

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.19

Np Likeness Score: 1.39

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