(S)-3-(2-(2-(4-(Benzyloxy)phenyl)-1-(cyclohexanecarboxamido)ethyl)-5-phenylthiazole-4-carboxamido)benzoic acid

ID: ALA2436030

PubChem CID: 73355491

Max Phase: Preclinical

Molecular Formula: C39H37N3O5S

Molecular Weight: 659.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(NC(=O)c2nc([C@H](Cc3ccc(OCc4ccccc4)cc3)NC(=O)C3CCCCC3)sc2-c2ccccc2)c1

Standard InChI:  InChI=1S/C39H37N3O5S/c43-36(29-15-8-3-9-16-29)41-33(23-26-19-21-32(22-20-26)47-25-27-11-4-1-5-12-27)38-42-34(35(48-38)28-13-6-2-7-14-28)37(44)40-31-18-10-17-30(24-31)39(45)46/h1-2,4-7,10-14,17-22,24,29,33H,3,8-9,15-16,23,25H2,(H,40,44)(H,41,43)(H,45,46)/t33-/m0/s1

Standard InChI Key:  RXDVRRLCEKEDMY-XIFFEERXSA-N

Molfile:  

     RDKit          2D

 48 53  0  0  0  0  0  0  0  0999 V2000
   10.5121   -8.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2198   -8.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9275   -8.8323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2198   -7.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6352   -8.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3429   -8.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6352   -7.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3429   -7.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4279   -9.6409    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.2272   -9.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6358   -9.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0890   -8.4959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0504   -7.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7576   -7.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7580   -6.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0453   -5.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3410   -6.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4485   -9.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9289   -9.6786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7416   -9.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8045   -8.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0989   -8.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0947   -9.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8022  -10.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5140   -9.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4652   -5.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1734   -6.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8806   -5.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5887   -6.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2954   -5.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2947   -5.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5815   -4.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8778   -5.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7809   -8.2710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2183  -10.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0302  -10.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3633   -9.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8783   -8.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0681   -8.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5103  -10.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1776  -11.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3231  -10.7476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5619  -10.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0798  -11.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4116  -11.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2251  -12.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7058  -11.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3714  -10.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  1
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  6  2  0
  8 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  8  1  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
  1 21  1  0
  1 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 15 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 18 34  2  0
 20 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 20  1  0
 36 40  1  0
 40 41  2  0
 40 42  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 46 47  1  0
 47 48  2  0
 48 43  1  0
 10 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2436030

   3-[[2-[(1S)-1-(cyclohexanecarbonylamino)-2-(4-phenylmethoxyphenyl)ethyl]-5-phenyl-1,3-thiazole-4-carbonyl]amino]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: 659.81

Molecular Weight (Monoisotopic): 659.2454

AlogP: 8.32

#Rotatable Bonds: 12

Polar Surface Area: 117.62

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.92

CX Basic pKa: ┄

CX LogP: 8.33

CX LogD: 5.13

Aromatic Rings: 5

Heavy Atoms: 48

QED Weighted: 0.12

Np Likeness Score: -0.97

References

1. Chen YT, Tang CL, Ma WP, Gao LX, Wei Y, Zhang W, Li JY, Li J, Nan FJ..  (2013)  Design, synthesis, and biological evaluation of novel 2-ethyl-5-phenylthiazole-4-carboxamide derivatives as protein tyrosine phosphatase 1B inhibitors with improved cellular efficacy.,  69  [PMID:24090912] [10.1016/j.ejmech.2013.09.017]

Source

Source(1):

• Scientific Literature