(3R,4S,5R)-5-{[(1S)-1-carboxylato-2,2-difluoro-1-(phosphonatooxy)ethyl]oxy}-4-hydroxy-3-[(hydroxyphosphinato)oxy]cyclohex-1-ene-1-carboxylate; Sodium

ID: ALA1627015

PubChem CID: 53322470

Max Phase: Preclinical

Molecular Formula: C10H13F2NaO14P2

Molecular Weight: 458.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])C1=C[C@@H](OP(=O)(O)O)[C@@H](O)[C@H](O[C@](OP(=O)(O)O)(C(=O)O)C(F)F)C1.[Na+]

Standard InChI:  InChI=1S/C10H14F2O14P2.Na/c11-8(12)10(9(16)17,26-28(21,22)23)24-4-1-3(7(14)15)2-5(6(4)13)25-27(18,19)20;/h2,4-6,8,13H,1H2,(H,14,15)(H,16,17)(H2,18,19,20)(H2,21,22,23);/q;+1/p-1/t4-,5-,6+,10-;/m1./s1

Standard InChI Key:  PHSVUZRDRYORKA-QIMFZATRSA-M

Molfile:  

     RDKit          2D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -1.2083   -3.8667    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.5125   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -2.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2375   -2.4875    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000   -4.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250   -4.1333    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2375   -4.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -4.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -4.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625   -3.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -3.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -3.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -4.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -5.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250   -4.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -4.9500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -5.3750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  1
  4  3  1  0
  5 12  1  0
  6  2  1  0
  7 16  1  0
  8 14  1  0
  9  6  1  1
 10  7  2  0
  2 11  1  6
 12  9  1  0
 13  7  1  0
  5 14  1  6
 15  2  1  0
 16  9  1  0
 17  4  2  0
 18  8  2  0
 19 13  1  0
 20 11  2  0
 21 13  2  0
 22  4  1  0
 23  4  1  0
 24  8  1  0
 25  8  1  0
 12 26  1  6
 27 11  1  0
 28 15  1  0
 29 15  1  0
  5 10  1  0
M  CHG  2   1   1  19  -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: 458.15

Molecular Weight (Monoisotopic): 457.9827

AlogP: -1.22

#Rotatable Bonds: 9

Polar Surface Area: 237.58

Molecular Species: ACID

HBA: 8

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.20

CX Basic pKa: ┄

CX LogP: -1.13

CX LogD: -15.40

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.16

Np Likeness Score: 1.05

References

1. Peterson ML, Corey SD, Font JL, Walker MC, Sikorski JA.  (1996)  New simplified inhibitors of EPSP synthase: The importance of ring size for recognition at the shikimate 3-phosphate site,  6  (23): [10.1016/S0960-894X(96)00527-6]

Source

Source(1):

• Scientific Literature