3-(5-((2-oxo-5-p-tolylfuran-3(2H)-ylidene)methyl)furan-2-yl)benzoic acid

ID: ALA2295999

PubChem CID: 1920904

Max Phase: Preclinical

Molecular Formula: C23H16O5

Molecular Weight: 372.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C2=C/C(=C\c3ccc(-c4cccc(C(=O)O)c4)o3)C(=O)O2)cc1

Standard InChI:  InChI=1S/C23H16O5/c1-14-5-7-15(8-6-14)21-13-18(23(26)28-21)12-19-9-10-20(27-19)16-3-2-4-17(11-16)22(24)25/h2-13H,1H3,(H,24,25)/b18-12+

Standard InChI Key:  LFMGAYSGKKKIHC-LDADJPATSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   18.4844  -19.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4833  -20.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1913  -20.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9010  -20.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8982  -19.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1896  -19.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7739  -19.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7737  -18.2192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0663  -19.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6071  -19.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3546  -19.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8999  -18.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4869  -18.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6878  -18.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8147  -17.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3302  -16.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5785  -15.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9144  -15.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2562  -15.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5136  -16.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3542  -15.6015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4793  -15.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3054  -14.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5275  -14.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9227  -15.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1011  -15.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8788  -16.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1436  -14.8729    0.0000 C   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
  7  8  1  0
  7  9  2  0
  1  7  1  0
 11 12  1  0
 10 11  2  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  5 10  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 17 21  2  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
 19 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2295999

   3-[5-[(E)-[5-(4-methylphenyl)-2-oxofuran-3-ylidene]methyl]furan-2-yl]benzoic 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: 372.38

Molecular Weight (Monoisotopic): 372.0998

AlogP: 4.93

#Rotatable Bonds: 4

Polar Surface Area: 76.74

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: ┄

CX LogP: 4.69

CX LogD: 1.50

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.39

References

1. Park H, Kyung A, Lee H, Kang S, Yoon T, Ryu SE, Jeong DG.  (2013)  Virtual screening and biochemical evaluation of the inhibitors of dual-specificity phosphatase 26,  22  (8): [10.1007/s00044-012-0405-3]

Source

Source(1):

• Scientific Literature