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

ID: ALA2017788

PubChem CID: 70691740

Max Phase: Preclinical

Molecular Formula: C15H26O12P2

Molecular Weight: 460.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](COP(=O)(O)O)OCCCc1ccccc1

Standard InChI:  InChI=1S/C15H26O12P2/c16-12(9-26-28(19,20)21)14(17)15(18)13(10-27-29(22,23)24)25-8-4-7-11-5-2-1-3-6-11/h1-3,5-6,12-18H,4,7-10H2,(H2,19,20,21)(H2,22,23,24)/t12-,13-,14-,15-/m1/s1

Standard InChI Key:  QZMYEEYVCDTZDF-KBUPBQIOSA-N

Molfile:  

     RDKit          2D

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   -1.6797   -3.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154   -3.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9617   -4.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797   -3.0593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9617   -5.1280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2480   -3.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -4.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2480   -3.0593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -5.1280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878   -3.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9057   -4.2997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333   -4.2997    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181   -3.8793    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082   -3.0510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409   -4.2827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340   -3.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5460   -3.8859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8353   -5.1239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5495   -4.7076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837   -5.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837   -6.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8973   -6.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8973   -7.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1817   -8.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813   -8.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8955   -9.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117   -8.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085   -8.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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  2  0
  3 13  1  0
 25 26  1  0
  4  7  1  0
 26 27  2  0
 12 14  1  0
 27 28  1  0
  2  4  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2017788

   [(2R,3R,4S,5R)-2,3,4-trihydroxy-5-(3-phenylpropoxy)-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: 460.31

Molecular Weight (Monoisotopic): 460.0899

AlogP: -0.69

#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: -0.88

CX LogD: -7.70

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.14

Np Likeness Score: 0.64

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