(3R,4R,5R)-5-Carboxymethoxy-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid; trisodium salt

ID: ALA88396

PubChem CID: 44321861

Max Phase: Preclinical

Molecular Formula: C9H10Na3O10P

Molecular Weight: 312.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])CO[C@@H]1CC(C(=O)[O-])=C[C@@H](OP(=O)([O-])O)[C@@H]1O.[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C9H13O10P.3Na/c10-7(11)3-18-5-1-4(9(13)14)2-6(8(5)12)19-20(15,16)17;;;/h2,5-6,8,12H,1,3H2,(H,10,11)(H,13,14)(H2,15,16,17);;;/q;3*+1/p-3/t5-,6-,8-;;;/m1.../s1

Standard InChI Key:  XLGYOVWWJFRDAD-VOXFAHSRSA-K

Molfile:  

     RDKit          2D

 23 20  0  0  0  0  0  0  0  0999 V2000
    9.6500   -0.8542    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.2667    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -0.5917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750    2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500    0.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -0.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -1.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042    0.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875    3.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542    3.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292   -0.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500    0.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -1.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -0.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3542    3.6250    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    2.3000   -1.2125    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  3  8  1  0
  4  5  2  0
  5  2  1  0
  6  2  1  0
  7  4  1  0
  2  8  1  6
  9  6  1  0
 10  9  1  0
 11 20  1  0
 12  3  1  0
 13  3  2  0
  9 14  1  1
 15  7  1  0
 16  7  2  0
 17 11  1  0
 18 11  2  0
 19  3  1  0
 20 14  1  0
  6 21  1  1
  4 10  1  0
M  CHG  6   1   1  12  -1  15  -1  17  -1  22   1  23   1
M  END

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: 312.17

Molecular Weight (Monoisotopic): 312.0246

AlogP: -1.29

#Rotatable Bonds: 6

Polar Surface Area: 170.82

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.31

CX Basic pKa: ┄

CX LogP: -1.64

CX LogD: -11.55

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.37

Np Likeness Score: 1.41

References

1. Miller MJ, Braccolino DS, Clearly DG, Ream JE, Walker MC, Sikorski JA.  (1994)  EPSP synthase inhibitor design IV. New aromatic substrate analogs and symmetrical inhibitors containing novel 3-phosphate mimics.,  4  (21): [10.1016/S0960-894X(01)80293-6]

Source

Source(1):

• Scientific Literature