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

ID: ALA1761646

PubChem CID: 54582322

Max Phase: Preclinical

Molecular Formula: C24H27Cl2NO3

Molecular Weight: 448.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C[C@H](c2ccccc2Cl)c2cc(Cl)ccc2[C@@H](CC(C)C)C1=O

Standard InChI:  InChI=1S/C24H27Cl2NO3/c1-4-30-23(28)14-27-13-21(18-7-5-6-8-22(18)26)19-12-16(25)9-10-17(19)20(24(27)29)11-15(2)3/h5-10,12,15,20-21H,4,11,13-14H2,1-3H3/t20-,21-/m1/s1

Standard InChI Key:  TUGVWLAGOWTNBY-NHCUHLMSSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.6958    0.1808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2898    0.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    1.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3399   -0.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207   -0.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8346   -0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8326    0.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1314    0.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311    0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370   -0.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393   -0.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3286   -1.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607   -1.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9810    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8510    0.9921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5257    1.7112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2721    1.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    2.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572    3.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8621    3.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721    2.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4807    2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    0.9753    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -1.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3009   -2.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6568    2.2414    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3062    0.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1762    0.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1  2  1  0
 16 29  1  0
  1 14  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761646

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

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: 448.39

Molecular Weight (Monoisotopic): 447.1368

AlogP: 5.66

#Rotatable Bonds: 6

Polar Surface Area: 46.61

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.70

CX LogD: 5.70

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: -0.43

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