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

ID: ALA1627010

PubChem CID: 53326392

Max Phase: Preclinical

Molecular Formula: C10H12F3NaO14P2

Molecular Weight: 476.14

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)F)C1.[Na+]

Standard InChI:  InChI=1S/C10H13F3O14P2.Na/c11-10(12,13)9(8(17)18,27-29(22,23)24)25-4-1-3(7(15)16)2-5(6(4)14)26-28(19,20)21;/h2,4-6,14H,1H2,(H,15,16)(H,17,18)(H2,19,20,21)(H2,22,23,24);/q;+1/p-1/t4-,5-,6+,9+;/m1./s1

Standard InChI Key:  COJXFWPMJUITPC-YWJASCBZSA-M

Molfile:  

     RDKit          2D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -1.0750   -3.7417    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.6417   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -2.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -2.3542    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -4.0042    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -3.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -3.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -3.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -1.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -4.8167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -5.2417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -5.1292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -1.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -1.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667   -4.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -4.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -4.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -4.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  1
  4  2  1  0
  5  3  1  0
  6 13  1  0
  7  2  1  0
  8 16  1  0
  9 15  1  0
 10  7  1  1
 11  8  2  0
  2 12  1  6
 13 10  1  0
 14  8  1  0
  6 15  1  6
 16 10  1  0
 17  5  2  0
 18  9  2  0
 19 14  1  0
 20 12  2  0
 21 14  2  0
 22  4  1  0
 23  4  1  0
 24  4  1  0
 25  5  1  0
 26  5  1  0
 27  9  1  0
 28  9  1  0
 13 29  1  6
 30 12  1  0
  6 11  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: 476.14

Molecular Weight (Monoisotopic): 475.9733

AlogP: -0.92

#Rotatable Bonds: 8

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: -0.42

CX Basic pKa: ┄

CX LogP: -0.64

CX LogD: -15.04

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.17

Np Likeness Score: 1.00

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