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

ID: ALA1627014

PubChem CID: 53317223

Max Phase: Preclinical

Molecular Formula: C10H14FNaO14P2

Molecular Weight: 440.16

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@](CF)(OP(=O)(O)O)C(=O)O)C1.[Na+]

Standard InChI:  InChI=1S/C10H15FO14P2.Na/c11-3-10(9(15)16,25-27(20,21)22)23-5-1-4(8(13)14)2-6(7(5)12)24-26(17,18)19;/h2,5-7,12H,1,3H2,(H,13,14)(H,15,16)(H2,17,18,19)(H2,20,21,22);/q;+1/p-1/t5-,6-,7+,10-;/m1./s1

Standard InChI Key:  OEQXOWGCWNPOLH-NDGFODGGSA-M

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
   -1.2625   -3.4917    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.5792   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -3.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -2.6042    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -4.2542    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -3.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -3.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -3.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -2.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -1.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -4.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -5.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -5.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -5.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -5.0792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  1
  4  3  1  0
  5 11  1  0
  6 15  1  0
  7 14  1  0
  8  6  2  0
  9 10  1  1
 10  2  1  0
 11  9  1  0
  2 12  1  6
 13  6  1  0
  5 14  1  6
 15  9  1  0
 16  4  2  0
 17  7  2  0
 18 13  1  0
 19 12  2  0
 20 13  2  0
 21  4  1  0
 22  4  1  0
 23  2  1  0
 24  7  1  0
 25  7  1  0
 11 26  1  6
 27 12  1  0
 28 23  1  0
  5  8  1  0
M  CHG  2   1   1  18  -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: 440.16

Molecular Weight (Monoisotopic): 439.9921

AlogP: -1.52

#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: -1.39

CX LogD: -15.49

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.16

Np Likeness Score: 1.17

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