trans-rac-6-(2-(7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)acetamido)hexanoic acid

ID: ALA1761657

PubChem CID: 54587204

Max Phase: Preclinical

Molecular Formula: C28H34Cl2N2O4

Molecular Weight: 533.50

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H34Cl2N2O4/c1-18(2)14-23-20-12-11-19(29)15-22(20)24(21-8-5-6-9-25(21)30)16-32(28(23)36)17-26(33)31-13-7-3-4-10-27(34)35/h5-6,8-9,11-12,15,18,23-24H,3-4,7,10,13-14,16-17H2,1-2H3,(H,31,33)(H,34,35)/t23-,24-/m1/s1

Standard InChI Key:  LFTDPLLBAFQCLO-DNQXCXABSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.6420  -20.0931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0457  -19.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8532  -19.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958  -20.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109  -21.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4932  -20.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4952  -19.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1929  -19.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8893  -19.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8834  -20.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1851  -20.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0020  -21.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780  -21.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764  -20.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635  -19.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4979  -19.2858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162  -18.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0581  -18.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704  -17.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6747  -17.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658  -16.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0525  -17.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450  -18.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6067  -19.3025    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8329  -22.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0239  -23.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727  -21.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806  -18.0431    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451  -20.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205  -20.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2333  -19.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988  -19.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516  -19.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4172  -19.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8699  -20.6700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300  -19.1707    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
 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
  6  7  2  0
 30 31  1  0
 14 15  1  0
 31 32  1  0
  2  3  1  0
 32 33  1  0
 15 16  1  0
 33 34  1  0
  7  8  1  0
 34 35  1  0
 15 17  2  0
 34 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761657

   trans-rac-6-(2-(7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)acetamido)hexanoic 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: 533.50

Molecular Weight (Monoisotopic): 532.1896

AlogP: 5.86

#Rotatable Bonds: 11

Polar Surface Area: 86.71

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.49

CX Basic pKa: ┄

CX LogP: 5.50

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.35

Np Likeness Score: -0.36

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