(1R,4R,5R)-3-(4-Fluoro-phenyl)-1,4,5-trihydroxy-cyclohex-2-enecarboxylic acid

ID: ALA362122

PubChem CID: 6480941

Max Phase: Preclinical

Molecular Formula: C13H13FO5

Molecular Weight: 268.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2ccc(F)cc2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C13H13FO5/c14-8-3-1-7(2-4-8)9-5-13(19,12(17)18)6-10(15)11(9)16/h1-5,10-11,15-16,19H,6H2,(H,17,18)/t10-,11-,13+/m1/s1

Standard InChI Key:  SYASNCLOYWGRTC-WZRBSPASSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  1  0  0  0  0  0999 V2000
    5.3542   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500    0.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -2.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000    0.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -3.2250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  7  1  0
  3  6  1  1
  7  4  1  0
  8  1  1  0
  9  6  2  0
 10  8  2  0
 11  8  1  0
  3 12  1  6
  4 13  1  6
 14  6  1  0
  7 15  1  1
 16 17  1  0
 17 11  2  0
 18 10  1  0
 19 16  1  0
 18 16  2  0
  5  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA362122

   (1R,4R,5R)-3-(4-Fluoro-phenyl)-1,4,5-trihydroxy-cyclohex-2-enecarboxylic 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: 268.24

Molecular Weight (Monoisotopic): 268.0747

AlogP: 0.15

#Rotatable Bonds: 2

Polar Surface Area: 97.99

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.42

CX Basic pKa: ┄

CX LogP: 0.06

CX LogD: -3.34

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.61

Np Likeness Score: 0.72

References

1. Sánchez-Sixto C, Prazeres VF, Castedo L, Lamb H, Hawkins AR, González-Bello C..  (2005)  Structure-based design, synthesis, and biological evaluation of inhibitors of Mycobacterium tuberculosis type II dehydroquinase.,  48  (15): [PMID:16033267] [10.1021/jm0501836]

Source

Source(1):

• Scientific Literature