4-(Hydroxy-phosphono-methyl)-1H-pyrrole-2-carboxylic acid

ID: ALA1160691

Max Phase: Preclinical

Molecular Formula: C6H8NO6P

Molecular Weight: 221.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(C(O)P(=O)(O)O)c[nH]1

Standard InChI:  InChI=1S/C6H8NO6P/c8-5(9)4-1-3(2-7-4)6(10)14(11,12)13/h1-2,6-7,10H,(H,8,9)(H2,11,12,13)

Standard InChI Key:  FUIBIIXRDPUFOF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    3.5792   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -3.3417    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -4.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -5.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -4.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -4.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -2.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -5.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -4.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -3.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  4  2  0
  4  1  1  0
  5  1  1  0
  6  7  1  0
  7  1  2  0
  8  3  1  0
  9  2  1  0
 10  2  2  0
 11  8  1  0
 12  8  2  0
 13  2  1  0
 14  5  1  0
  3  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160691

   ---

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: 221.10

Molecular Weight (Monoisotopic): 221.0089

AlogP: -0.12

#Rotatable Bonds: 3

Polar Surface Area: 130.85

Molecular Species: ACID

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.22

CX Basic pKa: ┄

CX LogP: -1.35

CX LogD: -7.18

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.45

Np Likeness Score: 0.55

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