5-(4-Chloro-2-hydroxyphenoxy)thiophene-2-carboxylic Acid

ID: ALA2347832

PubChem CID: 71579713

Max Phase: Preclinical

Molecular Formula: C11H7ClO4S

Molecular Weight: 270.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(Oc2ccc(Cl)cc2O)s1

Standard InChI:  InChI=1S/C11H7ClO4S/c12-6-1-2-8(7(13)5-6)16-10-4-3-9(17-10)11(14)15/h1-5,13H,(H,14,15)

Standard InChI Key:  VULPKDOAVISHKZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    0.5358  -15.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5347  -16.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2491  -16.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9652  -16.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9623  -15.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473  -14.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449  -14.0094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867  -16.4852    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6749  -14.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3902  -15.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3938  -16.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1780  -16.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6628  -15.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1782  -14.9869    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4898  -15.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9021  -16.3682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9022  -14.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  2  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
 15 16  1  0
 15 17  2  0
 13 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2347832

   5-(4-Chloro-2-hydroxy-phenoxy)thiophene-2-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: 270.69

Molecular Weight (Monoisotopic): 269.9754

AlogP: 3.60

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.35

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: -0.10

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.89

Np Likeness Score: -0.20

References

1. Cheng G, Muench SP, Zhou Y, Afanador GA, Mui EJ, Fomovska A, Lai BS, Prigge ST, Woods S, Roberts CW, Hickman MR, Lee PJ, Leed SE, Auschwitz JM, Rice DW, McLeod R..  (2013)  Design, synthesis, and biological activity of diaryl ether inhibitors of Toxoplasma gondii enoyl reductase.,  23  (7): [PMID:23453069] [10.1016/j.bmcl.2013.02.019]

Source

Source(1):

• Scientific Literature