1-(4-Bromobenzyl) alpha-3-hydroxycarbonyl-2,4-diphenylcyclobutane-1-carboxylate

ID: ALA4293553

PubChem CID: 130428466

Max Phase: Preclinical

Molecular Formula: C25H21BrO4

Molecular Weight: 465.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1[C@H](c2ccccc2)[C@H](C(=O)OCc2ccc(Br)cc2)[C@H]1c1ccccc1

Standard InChI:  InChI=1S/C25H21BrO4/c26-19-13-11-16(12-14-19)15-30-25(29)23-20(17-7-3-1-4-8-17)22(24(27)28)21(23)18-9-5-2-6-10-18/h1-14,20-23H,15H2,(H,27,28)/t20-,21-,22-,23-/m0/s1

Standard InChI Key:  TUIVMGPGCGTISM-MLCQCVOFSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   29.1217  -10.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1217  -11.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9389  -11.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9389  -10.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5439  -10.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7572   -9.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1801   -8.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3898   -9.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1798   -9.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7583  -10.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5439  -12.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7545  -11.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7554  -12.9151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5167  -10.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3061  -10.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3052   -9.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5167  -12.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3023  -12.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8793  -13.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6696  -13.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8797  -12.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3011  -11.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1775  -13.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3882  -13.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1789  -12.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3904  -12.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8116  -12.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0268  -13.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8149  -13.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0220  -12.6465    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  1  1  0
  1  5  1  1
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  1
 11 12  2  0
 11 13  1  0
  4 14  1  6
 14 15  1  0
 14 16  2  0
  3 17  1  6
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 13 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4293553

   ---

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: 465.34

Molecular Weight (Monoisotopic): 464.0623

AlogP: 5.39

#Rotatable Bonds: 6

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.23

CX Basic pKa: ┄

CX LogP: 5.70

CX LogD: 2.69

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -0.03

References

1. Yan S, Elmes MW, Tong S, Hu K, Awwa M, Teng GYH, Jing Y, Freitag M, Gan Q, Clement T, Wei L, Sweeney JM, Joseph OM, Che J, Carbonetti GS, Wang L, Bogdan DM, Falcone J, Smietalo N, Zhou Y, Ralph B, Hsu HC, Li H, Rizzo RC, Deutsch DG, Kaczocha M, Ojima I..  (2018)  SAR studies on truxillic acid mono esters as a new class of antinociceptive agents targeting fatty acid binding proteins.,  154  [PMID:29803996] [10.1016/j.ejmech.2018.04.050]

Source

Source(1):

• Scientific Literature