(2Z,4Z,6Z)-3-((E)-3-(2,4-dichlorophenyl)acryloyl)-2-hydroxycyclohepta-2,4,6-trienone

ID: ALA4474974

PubChem CID: 24824991

Max Phase: Preclinical

Molecular Formula: C16H10Cl2O3

Molecular Weight: 321.16

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(Cl)cc1Cl)c1ccccc(=O)c1O

Standard InChI:  InChI=1S/C16H10Cl2O3/c17-11-7-5-10(13(18)9-11)6-8-14(19)12-3-1-2-4-15(20)16(12)21/h1-9H,(H,20,21)/b8-6+

Standard InChI Key:  MYAQWRGPXRLRGL-SOFGYWHQSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   22.1855   -1.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3573   -1.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9776   -2.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7883   -2.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7113   -3.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0003   -3.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2594   -3.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5521   -1.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4219   -0.8992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4102   -3.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3930   -4.2945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1264   -3.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8253   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5415   -3.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2367   -3.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9524   -3.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9701   -2.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2662   -1.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5534   -2.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2180   -4.3551    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.6858   -1.9328    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  7  3  1  0
  4  5  2  0
  4  8  1  0
  1  9  2  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 15 20  1  0
 17 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474974

   3-[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]-2-hydroxycyclohepta-2,4,6-trien-1-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 321.16

Molecular Weight (Monoisotopic): 320.0007

AlogP: 3.96

#Rotatable Bonds: 3

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 4.42

CX LogD: 4.40

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -0.26

References

1. Ge L, Li KS, Li MM, Xiao P, Hou XB, Chen X, Liu HD, Lin A, Yu X, Ren GJ, Fang H, Sun JP..  (2016)  Identification of a benzo imidazole thiazole derivative as the specific irreversible inhibitor of protein tyrosine phosphatase.,  26  (19): [PMID:27554446] [10.1016/j.bmcl.2016.08.024]

Source

Source(1):

• Scientific Literature