tert-Butyl 4-[5-(4-Chloro-2-hydroxyphenoxy)thiophene-2-carbonyl]piperazine-1-carboxylate

ID: ALA2347831

PubChem CID: 71579903

Max Phase: Preclinical

Molecular Formula: C20H23ClN2O5S

Molecular Weight: 438.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N1CCN(C(=O)c2ccc(Oc3ccc(Cl)cc3O)s2)CC1

Standard InChI:  InChI=1S/C20H23ClN2O5S/c1-20(2,3)28-19(26)23-10-8-22(9-11-23)18(25)16-6-7-17(29-16)27-15-5-4-13(21)12-14(15)24/h4-7,12,24H,8-11H2,1-3H3

Standard InChI Key:  SCLMNRGNCLBCLI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.3921  -15.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1069  -15.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8233  -15.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8204  -14.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1051  -14.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1027  -13.3404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6774  -15.8173    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.5333  -14.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2489  -14.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2525  -15.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0370  -15.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5221  -14.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0372  -14.3183    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.3494  -14.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7618  -15.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7619  -14.2714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3470  -16.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7559  -17.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5811  -17.1294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9959  -16.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5854  -15.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9909  -17.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5756  -18.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8158  -17.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2255  -18.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0504  -18.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8102  -19.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6316  -19.2737    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
  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
 16 18  1  0
 16 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2347831

   Tert-butyl 4-[5-(4-chloro-2-hydroxy-phenoxy)thiophene-2-carbonyl]piperazine-1-carboxylate

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: 438.93

Molecular Weight (Monoisotopic): 438.1016

AlogP: 4.59

#Rotatable Bonds: 3

Polar Surface Area: 79.31

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.62

CX Basic pKa: ┄

CX LogP: 3.90

CX LogD: 3.70

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.76

Np Likeness Score: -0.87

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