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

ID: ALA1761647

PubChem CID: 54585229

Max Phase: Preclinical

Molecular Formula: C23H26ClNO3

Molecular Weight: 399.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)[C@@H](c1ccccc1Cl)CN(CC(=O)O)C(=O)[C@@H]2CC(C)C

Standard InChI:  InChI=1S/C23H26ClNO3/c1-14(2)10-19-16-9-8-15(3)11-18(16)20(17-6-4-5-7-21(17)24)12-25(23(19)28)13-22(26)27/h4-9,11,14,19-20H,10,12-13H2,1-3H3,(H,26,27)/t19-,20-/m1/s1

Standard InChI Key:  GDJRPHAADWFEKK-WOJBJXKFSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   13.4681    0.2475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0621    1.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2500    1.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1123   -0.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2925   -0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6064   -0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6044    0.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9027    1.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2024    0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2083   -0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9106   -0.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1004   -1.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6330   -1.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3386    0.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7538    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6243    1.0592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2985    1.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0440    1.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6350    2.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4295    3.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6339    3.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0439    2.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2525    2.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4857    1.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2648   -1.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0727   -2.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6214   -1.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4292    2.3091    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1 14  1  0
  6  7  2  0
 14 15  1  0
  2  3  1  0
 15 16  1  0
  7  8  1  0
 15 17  2  0
  1  4  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA1761647

   trans-rac-2-(5-(2-chlorophenyl)-1-isobutyl-7-methyl-2-oxo-4,5-dihydro-1H-benzo[d]azepin-3(2H)-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: 399.92

Molecular Weight (Monoisotopic): 399.1601

AlogP: 4.84

#Rotatable Bonds: 5

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.17

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 2.05

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.78

Np Likeness Score: -0.07

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