(1R,4R,5R)-1,4,5-Trihydroxy-3-pyridin-3-yl-cyclohex-2-enecarboxylic acid

ID: ALA425726

PubChem CID: 6480949

Max Phase: Preclinical

Molecular Formula: C12H13NO5

Molecular Weight: 251.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cccnc2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C12H13NO5/c14-9-5-12(18,11(16)17)4-8(10(9)15)7-2-1-3-13-6-7/h1-4,6,9-10,14-15,18H,5H2,(H,16,17)/t9-,10-,12+/m1/s1

Standard InChI Key:  UENDUKMAYCPERY-FOGDFJRCSA-N

Molfile:  

     RDKit          2D

 18 19  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
    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
    4.2375   -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
    2.8125   -3.1792    0.0000 N   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
    7.0917   -3.1792    0.0000 O   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   -4.0042    0.0000 C   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
    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  7  1  0
  3  6  1  1
  7  4  1  0
  8  1  1  0
  9  6  2  0
 10 15  1  0
  3 11  1  6
  4 12  1  6
 13  6  1  0
  7 14  1  1
 15  8  2  0
 16 18  1  0
 17  8  1  0
 18 17  2  0
  5  3  1  0
 10 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA425726

   (1R,4R,5R)-1,4,5-Trihydroxy-3-pyridin-3-yl-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: 251.24

Molecular Weight (Monoisotopic): 251.0794

AlogP: -0.59

#Rotatable Bonds: 2

Polar Surface Area: 110.88

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.22

CX Basic pKa: 4.70

CX LogP: -2.39

CX LogD: -4.62

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.56

Np Likeness Score: 0.83

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