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

ID: ALA2017791

PubChem CID: 70681220

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@@](O)(CCCc1ccccc1)COP(=O)(O)O

Standard InChI:  InChI=1S/C15H26O12P2/c16-12(9-26-28(20,21)22)13(17)14(18)15(19,10-27-29(23,24)25)8-4-7-11-5-2-1-3-6-11/h1-3,5-6,12-14,16-19H,4,7-10H2,(H2,20,21,22)(H2,23,24,25)/t12-,13-,14+,15-/m1/s1

Standard InChI Key:  PRWVTMLZUHQBPJ-APIJFGDWSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.7875    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0689    1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061    1.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0689    2.5958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    0.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358    1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785    1.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358    2.5958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    0.8049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8015    1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5202    1.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248    1.3542    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.2333    1.7750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.2234    2.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569    1.3712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500    2.1958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9382    1.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2268    0.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9417    0.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6583    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3665   -0.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -1.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467   -1.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6422   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0740   -2.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750   -1.7056    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
  8 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:

   

   ALA2017791

   [(2R,3R,4S,5R)-2,3,4,5-tetrahydroxy-8-phenyl-5-(phosphonooxymethyl)octyl] 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: -0.96

#Rotatable Bonds: 13

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: -1.15

CX LogD: -7.64

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.17

Np Likeness Score: 1.13

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