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

ID: ALA1761659

PubChem CID: 54587205

Max Phase: Preclinical

Molecular Formula: C28H32Cl2N2O4

Molecular Weight: 531.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H32Cl2N2O4/c1-17(2)13-23-20-8-7-19(29)14-22(20)24(21-5-3-4-6-25(21)30)15-32(27(23)34)16-26(33)31-11-9-18(10-12-31)28(35)36/h3-8,14,17-18,23-24H,9-13,15-16H2,1-2H3,(H,35,36)/t23-,24-/m1/s1

Standard InChI Key:  MJBBWPDFYUSKKR-DNQXCXABSA-N

Molfile:  

     RDKit          2D

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   18.8707  -19.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0632  -19.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9205  -21.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1054  -21.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4232  -20.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4213  -20.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7236  -19.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0272  -20.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.7314  -21.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9144  -22.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4383  -21.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1399  -20.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5527  -19.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4183  -19.6863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1000  -18.9713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8583  -18.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4460  -18.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2417  -17.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4506  -17.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640  -17.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0714  -18.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3146  -19.7030    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.0836  -22.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8926  -23.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4438  -21.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2356  -18.4436    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.8643  -20.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7262  -20.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1431  -19.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6916  -18.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8232  -18.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0090  -19.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4609  -20.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4266  -18.8626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  3 18  1  1
  8  9  2  0
 18 19  2  0
  5  6  1  0
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  9 10  1  0
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  7  3  1  0
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 10 11  2  0
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  9 24  1  0
  4  5  1  0
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  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
 15 17  2  0
 34 35  1  0
 34 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761659

   trans-rac-1-(2-(7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)acetyl)piperidine-4-carboxylic 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: 531.48

Molecular Weight (Monoisotopic): 530.1739

AlogP: 5.42

#Rotatable Bonds: 6

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: 4.04

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 1.77

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.54

Np Likeness Score: -0.59

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