trans-rac-2-(1-(2-(7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)acetyl)piperidin-4-yl)acetic acid

ID: ALA1761658

PubChem CID: 54582325

Max Phase: Preclinical

Molecular Formula: C29H34Cl2N2O4

Molecular Weight: 545.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H]1C(=O)N(CC(=O)N2CCC(CC(=O)O)CC2)C[C@H](c2ccccc2Cl)c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C29H34Cl2N2O4/c1-18(2)13-24-21-8-7-20(30)15-23(21)25(22-5-3-4-6-26(22)31)16-33(29(24)37)17-27(34)32-11-9-19(10-12-32)14-28(35)36/h3-8,15,18-19,24-25H,9-14,16-17H2,1-2H3,(H,35,36)/t24-,25-/m1/s1

Standard InChI Key:  SJYICAYPBJXIFV-JWQCQUIFSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
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    8.2529  -18.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4454  -18.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3028  -20.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4877  -20.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8054  -20.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8034  -19.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1057  -18.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4093  -19.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4152  -20.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1135  -20.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2966  -21.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8206  -21.0621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5223  -19.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9351  -18.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8007  -18.8508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4824  -18.1357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2406  -17.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8282  -17.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6239  -16.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8328  -16.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461  -16.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536  -17.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6966  -18.8675    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.4657  -21.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747  -22.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8260  -21.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6180  -17.6080    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2469  -19.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1087  -19.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5257  -18.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0742  -18.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2057  -18.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3917  -18.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8418  -19.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4281  -20.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7100  -19.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3 18  1  1
  8  9  2  0
 18 19  2  0
  5  6  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
  7  3  1  0
 21 22  1  0
 10 11  2  0
 22 23  2  0
 23 18  1  0
 11  6  1  0
  9 24  1  0
  4  5  1  0
 12 25  1  0
  5 12  1  6
 25 26  1  0
 25 27  1  0
  4 13  2  0
 19 28  1  0
 16 29  1  0
  1  2  1  0
  1 14  1  0
  6  7  2  0
 14 15  1  0
  2  3  1  0
 16 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 15 16  1  0
 31 34  1  0
  7  8  1  0
 34 35  1  0
 15 17  2  0
  1  4  1  0
 35 36  1  0
 35 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761658

   trans-rac-2-(1-(2-(7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)acetyl)piperidin-4-yl)acetic 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: 545.51

Molecular Weight (Monoisotopic): 544.1896

AlogP: 5.81

#Rotatable Bonds: 7

Polar Surface Area: 77.92

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.30

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 2.13

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.48

Np Likeness Score: -0.52

References

1. Griebenow N, Flessner T, Buchmueller A, Raabe M, Bischoff H, Kolkhof P..  (2011)  Identification and optimization of tetrahydro-2H-3-benzazepin-2-ones as squalene synthase inhibitors.,  21  (8): [PMID:21396815] [10.1016/j.bmcl.2011.02.004]

2. Soltis, D A DA and 9 more authors.  1995-02-01  Expression, purification, and characterization of the human squalene synthase: use of yeast and baculoviral systems.  [PMID:7864626]

3. Cammerer, Simon B SB and 14 more authors.  2007-11  Quinuclidine derivatives as potential antiparasitics.  [PMID:17709461]

4. Song, Yongcheng and 11 more authors.  2009-02-26  Phosphonosulfonates are potent, selective inhibitors of dehydrosqualene synthase and staphyloxanthin biosynthesis in Staphylococcus aureus.  [PMID:19191557]

5. Lin, Fu-Yang and 7 more authors.  2012-05-10  Head-to-head prenyl tranferases: anti-infective drug targets.  [PMID:22486710]

Source

Source(1):

• Scientific Literature