3-((3R,5R,6R)-3-Carboxy-3,5,6-trihydroxy-cyclohex-1-enyl)-benzoic acid

ID: ALA190424

PubChem CID: 6480946

Max Phase: Preclinical

Molecular Formula: C14H14O7

Molecular Weight: 294.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(C2=C[C@@](O)(C(=O)O)C[C@@H](O)[C@@H]2O)c1

Standard InChI:  InChI=1S/C14H14O7/c15-10-6-14(21,13(19)20)5-9(11(10)16)7-2-1-3-8(4-7)12(17)18/h1-5,10-11,15-16,21H,6H2,(H,17,18)(H,19,20)/t10-,11-,14+/m1/s1

Standard InChI Key:  UHMJIKHXQKZWMY-GYSYKLTISA-N

Molfile:  

     RDKit          2D

 21 22  0  0  1  0  0  0  0  0999 V2000
    4.9542   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -0.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -4.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -4.4167    0.0000 C   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  8  1  0
  6  1  1  0
  3  7  1  1
  8  4  1  0
  9 11  1  0
 10  6  2  0
 11 10  1  0
 12  7  2  0
 13  9  2  0
  3 14  1  6
  4 15  1  6
 16  7  1  0
 17  9  1  0
  8 18  1  1
 19  6  1  0
 20 21  1  0
 21 19  2  0
  5  3  1  0
 11 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA190424

   3-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxy-cyclohexen-1-yl]benzoic 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: 294.26

Molecular Weight (Monoisotopic): 294.0740

AlogP: -0.29

#Rotatable Bonds: 3

Polar Surface Area: 135.29

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.10

CX Basic pKa: ┄

CX LogP: -0.42

CX LogD: -7.04

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.52

Np Likeness Score: 0.89

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