2-[5-Carboxy-3-(carboxy-phosphono-methoxy)-2-hydroxy-phenyl]-2-hydroxy-malonic acid

ID: ALA98868

PubChem CID: 44328706

Max Phase: Preclinical

Molecular Formula: C12H11O14P

Molecular Weight: 410.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(OC(C(=O)O)P(=O)(O)O)c(O)c(C(O)(C(=O)O)C(=O)O)c1

Standard InChI:  InChI=1S/C12H11O14P/c13-6-4(12(22,10(18)19)11(20)21)1-3(7(14)15)2-5(6)26-9(8(16)17)27(23,24)25/h1-2,9,13,22H,(H,14,15)(H,16,17)(H,18,19)(H,20,21)(H2,23,24,25)

Standard InChI Key:  WNCBGKJMSWDKGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    3.9667   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5417   -4.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5417   -3.7750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -4.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -5.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -3.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2625   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -2.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -3.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -3.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9750   -4.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -2.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -5.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667   -3.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5542   -2.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -5.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -4.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -6.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2625   -5.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -2.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  3  1  0
  5  7  2  0
  6  5  1  0
  7  2  1  0
  8  2  2  0
  9  8  1  0
 10  1  1  0
 11  1  1  0
 12  3  1  0
 13  9  1  0
 14  9  2  0
 15  4  2  0
 16 10  2  0
 17 11  2  0
 18 12  2  0
 19 13  2  0
 20  1  1  0
 21  4  1  0
 22  4  1  0
 23  7  1  0
 24 10  1  0
 25 11  1  0
 26 12  1  0
 27 13  1  0
 14  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA98868

   2-[5-Carboxy-3-[carboxy(phosphono)methoxy]-2-hydroxyphenyl]-2-hydroxypropanedioic acid

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: 410.18

Molecular Weight (Monoisotopic): 409.9886

AlogP: -1.59

#Rotatable Bonds: 8

Polar Surface Area: 256.42

Molecular Species: ACID

HBA: 8

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.03

CX Basic pKa: ┄

CX LogP: -1.71

CX LogD: -17.48

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.18

Np Likeness Score: 0.43

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