(2R,3R,4S,5R)-2,3,4-trihydroxy-5-(pentyloxy)hexane-1,6-diyl bis(dihydrogen phosphate)

ID: ALA2017787

PubChem CID: 70689613

Max Phase: Preclinical

Molecular Formula: C11H26O12P2

Molecular Weight: 412.27

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H26O12P2/c1-2-3-4-5-21-9(7-23-25(18,19)20)11(14)10(13)8(12)6-22-24(15,16)17/h8-14H,2-7H2,1H3,(H2,15,16,17)(H2,18,19,20)/t8-,9-,10-,11-/m1/s1

Standard InChI Key:  JVJACORASAJWCM-GWOFURMSSA-N

Molfile:  

     RDKit          2D

 25 24  0  0  0  0  0  0  0  0999 V2000
   17.3166    0.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0321    1.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6010    1.0496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7476    0.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0321    1.8752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7476   -0.1867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4590    1.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1746    0.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4590    1.8752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1746   -0.1867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8901    1.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6056    0.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8855    0.6389    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.3157    1.0579    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.3057    1.8834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0362    0.6559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0293    1.4769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1752    1.0514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8834   -0.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1717    0.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8802   -0.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5897   -0.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2991   -0.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0085   -0.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7179   -0.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  4  6  1  6
 22 23  1  0
 11 12  1  0
 23 24  1  0
  1  2  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2017787

   [(2R,3R,4S,5R)-2,3,4-trihydroxy-5-pentoxy-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: 412.27

Molecular Weight (Monoisotopic): 412.0899

AlogP: -1.14

#Rotatable Bonds: 14

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: -1.57

CX LogD: -8.39

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.13

Np Likeness Score: 0.88

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