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

ID: ALA1761654

PubChem CID: 54581312

Max Phase: Preclinical

Molecular Formula: C22H23BrClNO3

Molecular Weight: 464.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H]1C(=O)N(CC(=O)O)C[C@H](c2ccccc2Br)c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C22H23BrClNO3/c1-13(2)9-18-15-8-7-14(24)10-17(15)19(16-5-3-4-6-20(16)23)11-25(22(18)28)12-21(26)27/h3-8,10,13,18-19H,9,11-12H2,1-2H3,(H,26,27)/t18-,19-/m1/s1

Standard InChI Key:  FIXFRXKZQMMDHW-RTBURBONSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.5594  -13.9307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1534  -13.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3414  -13.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2035  -14.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3839  -14.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978  -14.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958  -13.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9942  -13.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2939  -13.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2998  -14.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021  -14.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1918  -15.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7243  -15.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4299  -13.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8450  -13.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7155  -13.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3898  -12.3999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1353  -12.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7264  -11.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5209  -10.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253  -10.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354  -11.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3440  -12.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773  -13.1358    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3563  -16.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642  -16.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128  -15.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5204  -11.8693    0.0000 Br  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:

   

   ALA1761654

   trans-rac-2-(5-(2-bromophenyl)-7-chloro-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: 464.79

Molecular Weight (Monoisotopic): 463.0550

AlogP: 5.29

#Rotatable Bonds: 5

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.54

CX Basic pKa: ┄

CX LogP: 5.36

CX LogD: 2.00

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.09

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