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

ID: ALA361695

PubChem CID: 6480940

Max Phase: Preclinical

Molecular Formula: C13H14O5

Molecular Weight: 250.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2ccccc2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C13H14O5/c14-10-7-13(18,12(16)17)6-9(11(10)15)8-4-2-1-3-5-8/h1-6,10-11,14-15,18H,7H2,(H,16,17)/t10-,11-,13+/m1/s1

Standard InChI Key:  AYGIVMMGRZDUTI-WZRBSPASSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  1  0  0  0  0  0999 V2000
    4.4167   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5375    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125    0.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -2.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625    0.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -2.8125    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
  3 10  1  6
  4 11  1  6
 12  6  1  0
  7 13  1  1
 14  8  2  0
 15  8  1  0
 16 15  2  0
 17 14  1  0
 18 16  1  0
  5  3  1  0
 17 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA361695

   (1R,4R,5R)-1,4,5-Trihydroxy-3-phenyl-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: 250.25

Molecular Weight (Monoisotopic): 250.0841

AlogP: 0.01

#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: 3.65

CX Basic pKa: ┄

CX LogP: -0.08

CX LogD: -3.41

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.59

Np Likeness Score: 1.16

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