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

ID: ALA1823557

PubChem CID: 24857914

Max Phase: Preclinical

Molecular Formula: C11H12O5S

Molecular Weight: 256.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cccs2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C11H12O5S/c12-7-5-11(16,10(14)15)4-6(9(7)13)8-2-1-3-17-8/h1-4,7,9,12-13,16H,5H2,(H,14,15)/t7-,9-,11+/m1/s1

Standard InChI Key:  WVCLOPJCJZRGSN-ZOFUNIGCSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -1.8708   -7.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -8.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418   -7.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -8.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -9.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505   -9.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385   -9.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385   -8.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -7.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4565   -6.7468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246   -9.8344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505  -10.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -9.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6574   -9.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1557  -10.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6842  -10.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8947  -10.6595    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  9  1  0
  2  3  1  1
  3 10  2  0
  4  5  2  0
  7 11  1  1
  6 12  1  6
 13 14  2  0
  4  2  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  2  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
  5 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1823557

   (1R,4R,5R)-1,4,5-trihydroxy-3-thiophen-2-ylcyclohex-2-ene-1-carboxylic 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: 256.28

Molecular Weight (Monoisotopic): 256.0405

AlogP: 0.07

#Rotatable Bonds: 2

Polar Surface Area: 97.99

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.94

CX Basic pKa: ┄

CX LogP: -0.17

CX LogD: -3.36

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.60

Np Likeness Score: 0.57

References

1. Tizón L, Otero JM, Prazeres VF, Llamas-Saiz AL, Fox GC, van Raaij MJ, Lamb H, Hawkins AR, Ainsa JA, Castedo L, González-Bello C..  (2011)  A prodrug approach for improving antituberculosis activity of potent Mycobacterium tuberculosis type II dehydroquinase inhibitors.,  54  (17): [PMID:21780742] [10.1021/jm2006063]

Source

Source(1):

• Scientific Literature