6-Hydroxy-2-phenyl-3-((4-(trifluoromethoxy)phenyl)-ethynyl)benzofuran-5-carboxylic Acid

ID: ALA2316907

PubChem CID: 70982811

Max Phase: Preclinical

Molecular Formula: C24H13F3O5

Molecular Weight: 438.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(C#Cc3ccc(OC(F)(F)F)cc3)c(-c3ccccc3)oc2cc1O

Standard InChI:  InChI=1S/C24H13F3O5/c25-24(26,27)32-16-9-6-14(7-10-16)8-11-17-18-12-19(23(29)30)20(28)13-21(18)31-22(17)15-4-2-1-3-5-15/h1-7,9-10,12-13,28H,(H,29,30)

Standard InChI Key:  CMOKPKRDZUEWNH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.6478  -15.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288  -14.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256  -14.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474  -14.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0564  -14.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8577  -14.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9439  -13.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1959  -13.5723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6529  -13.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3606  -13.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0681  -13.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6084  -14.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6058  -16.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317  -17.0090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6762  -16.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5038  -17.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1099  -17.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8882  -17.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0571  -16.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4496  -16.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4959  -18.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3265  -18.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9340  -19.3467    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.5494  -19.0533    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1514  -19.5954    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
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  5  6  2  0
  6  7  1  0
  7  8  2  0
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  9  5  1  0
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 15 10  1  0
  8 10  1  0
  7 16  1  0
 16 17  3  0
  4 18  1  0
 19 20  1  0
 19 21  2  0
  1 19  1  0
 17 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2316907

   6-Hydroxy-2-phenyl-3-[2-[4-(trifluoromethoxy)phenyl]ethynyl]benzofuran-5-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: 438.36

Molecular Weight (Monoisotopic): 438.0715

AlogP: 5.80

#Rotatable Bonds: 3

Polar Surface Area: 79.90

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.35

CX Basic pKa: ┄

CX LogP: 7.26

CX LogD: 3.84

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -0.23

References

1. He Y, Xu J, Yu ZH, Gunawan AM, Wu L, Wang L, Zhang ZY..  (2013)  Discovery and evaluation of novel inhibitors of mycobacterium protein tyrosine phosphatase B from the 6-Hydroxy-benzofuran-5-carboxylic acid scaffold.,  56  (3): [PMID:23305444] [10.1021/jm301781p]

2. He Y, Liu S, Menon A, Stanford S, Oppong E, Gunawan AM, Wu L, Wu DJ, Barrios AM, Bottini N, Cato AC, Zhang ZY..  (2013)  A potent and selective small-molecule inhibitor for the lymphoid-specific tyrosine phosphatase (LYP), a target associated with autoimmune diseases.,  56  (12): [PMID:23713581] [10.1021/jm400248c]

Source

Source(1):

• Scientific Literature