(1R,4R,5R)-3-Furan-3-yl-1,4,5-trihydroxy-cyclohex-2-enecarboxylic acid

ID: ALA365959

PubChem CID: 6483679

Max Phase: Preclinical

Molecular Formula: C11H12O6

Molecular Weight: 240.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2ccoc2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C11H12O6/c12-8-4-11(16,10(14)15)3-7(9(8)13)6-1-2-17-5-6/h1-3,5,8-9,12-13,16H,4H2,(H,14,15)/t8-,9-,11+/m1/s1

Standard InChI Key:  NCNFPCUXYZKRRC-KKZNHRDASA-N

Molfile:  

     RDKit          2D

 17 18  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
    4.2375   -3.1792    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
    2.9292   -3.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -4.0000    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
    3.3500   -4.1750    0.0000 C   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
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  1  1  0
  6  8  1  0
  3  7  1  1
  8  4  1  0
  9 10  1  0
 10  5  2  0
 11  5  1  0
 12  7  2  0
 13 11  2  0
  3 14  1  6
  4 15  1  6
 16  7  1  0
  8 17  1  1
  9 13  1  0
  6  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA365959

   (1R,4R,5R)-3-Furan-3-yl-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: 240.21

Molecular Weight (Monoisotopic): 240.0634

AlogP: -0.40

#Rotatable Bonds: 2

Polar Surface Area: 111.13

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.60

CX Basic pKa: ┄

CX LogP: -0.94

CX LogD: -4.29

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.56

Np Likeness Score: 1.52

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