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

ID: ALA1761649

PubChem CID: 54585230

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](c2ccccc2Cl)c2ccccc21

Standard InChI:  InChI=1S/C22H24ClNO3/c1-14(2)11-18-15-7-3-4-8-16(15)19(17-9-5-6-10-20(17)23)12-24(22(18)27)13-21(25)26/h3-10,14,18-19H,11-13H2,1-2H3,(H,25,26)/t18-,19+/m1/s1

Standard InChI Key:  TVOUXWGXFQPNJZ-MOPGFXCFSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -1.9946   -6.8780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4006   -6.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128   -5.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3504   -7.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1703   -7.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8564   -7.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -6.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602   -6.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2605   -6.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2546   -7.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5523   -7.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3624   -8.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8296   -8.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1240   -6.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7088   -6.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1618   -6.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641   -5.3470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4188   -5.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277   -4.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332   -3.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8289   -3.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4189   -4.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102   -4.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1980   -8.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901   -9.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8415   -8.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -4.8163    0.0000 Cl  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
 12 24  1  0
  4  5  1  0
 24 25  1  0
  5 12  1  6
 24 26  1  0
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761649

   trans-rac-2-(5-(2-chlorophenyl)-1-isobutyl-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: 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: 1.49

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

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