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

ID: ALA1761653

PubChem CID: 54580309

Max Phase: Preclinical

Molecular Formula: C22H24ClNO3

Molecular Weight: 385.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H]1C(=O)N(CC(=O)O)C[C@H](c2ccccc2)c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C22H24ClNO3/c1-14(2)10-19-17-9-8-16(23)11-18(17)20(15-6-4-3-5-7-15)12-24(22(19)27)13-21(25)26/h3-9,11,14,19-20H,10,12-13H2,1-2H3,(H,25,26)/t19-,20-/m1/s1

Standard InChI Key:  CUKQKKMMMTUVHO-WOJBJXKFSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -1.7819  -13.4611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879  -12.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000  -12.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378  -14.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575  -14.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436  -13.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6456  -13.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3473  -12.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477  -13.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0418  -13.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394  -14.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496  -15.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6170  -14.8731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114  -13.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4962  -12.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3743  -12.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515  -11.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061  -11.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150  -11.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8205  -10.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6162  -10.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061  -10.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9974  -11.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7644  -12.6660    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852  -15.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773  -16.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6287  -14.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 13  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA1761653

   trans-rac-2-(7-chloro-1-isobutyl-2-oxo-5-phenyl-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: 385.89

Molecular Weight (Monoisotopic): 385.1445

AlogP: 4.53

#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: 4.10

CX Basic pKa: ┄

CX LogP: 4.59

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -0.02

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