(S)-3-(2-bromophenyl)-2-(2-(4-methoxyphenyl)acetamido)-N-((S)-1-phenylethyl)propanamide

ID: ALA4089982

PubChem CID: 118987011

Max Phase: Preclinical

Molecular Formula: C26H27BrN2O3

Molecular Weight: 495.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC(=O)N[C@@H](Cc2ccccc2Br)C(=O)N[C@@H](C)c2ccccc2)cc1

Standard InChI:  InChI=1S/C26H27BrN2O3/c1-18(20-8-4-3-5-9-20)28-26(31)24(17-21-10-6-7-11-23(21)27)29-25(30)16-19-12-14-22(32-2)15-13-19/h3-15,18,24H,16-17H2,1-2H3,(H,28,31)(H,29,30)/t18-,24-/m0/s1

Standard InChI Key:  ZFUNKFOMZPXBEZ-UUOWRZLLSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    4.8522   -8.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511   -9.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591  -10.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2688   -9.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2659   -8.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5573   -8.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9721   -8.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6813   -8.7985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9690   -7.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3875   -8.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967   -8.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3844   -7.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0998   -9.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8029   -8.3819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5122   -8.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2183   -8.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5152   -9.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3937  -10.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6849   -9.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9793  -10.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9819  -10.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6961  -11.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3989  -10.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2152   -7.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9224   -7.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9196   -6.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2099   -5.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5014   -6.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5076   -7.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1094  -11.2392    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.2045   -5.1150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4947   -4.7100    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
  5  7  1  0
  7  8  1  0
  7  9  1  6
  8 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  1
 11 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 16 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
 23 30  1  0
 31 32  1  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089982

   ---

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: 495.42

Molecular Weight (Monoisotopic): 494.1205

AlogP: 4.61

#Rotatable Bonds: 9

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.34

CX Basic pKa: ┄

CX LogP: 4.90

CX LogD: 4.90

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -0.79

References

1. Granchi C, Fortunato S, Minutolo F..  (2016)  Anticancer agents interacting with membrane glucose transporters.,  7  (9): [PMID:28042452] [10.1039/C6MD00287K]

Source

Source(1):

• Scientific Literature