2,3,4-trihydroxy-5-oxohexane-1,6-diyl bis(dihydrogen phosphate)

ID: ALA1235112

Max Phase: Preclinical

Molecular Formula: C6H14O12P2

Molecular Weight: 340.11

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H14O12P2/c7-3(1-17-19(11,12)13)5(9)6(10)4(8)2-18-20(14,15)16/h3,5-7,9-10H,1-2H2,(H2,11,12,13)(H2,14,15,16)/t3-,5-,6-/m1/s1

Standard InChI Key:  XPYBSIWDXQFNMH-UYFOZJQFSA-N

Molfile:  

     RDKit          2D

 20 19  0  0  0  0  0  0  0  0999 V2000
   -3.2030   -0.2731    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9175   -0.6856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905   -0.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6155    0.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4885    0.1394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7741   -0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596    0.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596    0.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3451   -0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3451   -1.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693    0.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693    0.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838   -0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838   -1.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7983    0.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128   -0.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272    0.1394    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417    0.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147    0.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6397   -0.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0
  2  1  1  0
  5  1  1  0
  3  1  1  0
  6  5  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  9 11  1  0
  9 10  1  6
 11 13  1  0
 11 12  1  6
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 18 17  2  0
 20 17  1  0
 19 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1235112

   ---

Molecule Features

Natural Product: Yes

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: 340.11

Molecular Weight (Monoisotopic): 339.9960

AlogP: -3.14

#Rotatable Bonds: 9

Polar Surface Area: 211.28

Molecular Species: ACID

HBA: 8

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.01

CX Basic pKa: ┄

CX LogP: -3.51

CX LogD: -10.38

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.21

Np Likeness Score: 1.20

References

1. Daher R, Coinçon M, Fonvielle M, Gest PM, Guerin ME, Jackson M, Sygusch J, Therisod M..  (2010)  Rational design, synthesis, and evaluation of new selective inhibitors of microbial class II (zinc dependent) fructose bis-phosphate aldolases.,  53  (21): [PMID:20929256] [10.1021/jm1009814]

2. 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]

3. Xu Y, Liu XH, Saunders M, Pearce S, Foulks JM, Parnell KM, Clifford A, Nix RN, Bullough J, Hendrickson TF, Wright K, McCullar MV, Kanner SB, Ho KK..  (2014)  Discovery of 3-(trifluoromethyl)-1H-pyrazole-5-carboxamide activators of the M2 isoform of pyruvate kinase (PKM2).,  24  (2): [PMID:24374270] [10.1016/j.bmcl.2013.12.028]

Source

Source(1):

• Scientific Literature