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

ID: ALA1761651

PubChem CID: 54582323

Max Phase: Preclinical

Molecular Formula: C22H23Cl2NO4

Molecular Weight: 436.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H23Cl2NO4/c1-22(2,29)10-17-14-8-7-13(23)9-16(14)18(15-5-3-4-6-19(15)24)11-25(21(17)28)12-20(26)27/h3-9,17-18,29H,10-12H2,1-2H3,(H,26,27)/t17-,18-/m1/s1

Standard InChI Key:  AEXOQRGCWFLFBD-QZTJIDSGSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   13.5515   -6.7359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1455   -5.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3334   -5.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1956   -7.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -7.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6897   -7.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6878   -6.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9860   -5.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2858   -6.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2917   -7.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9940   -7.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1838   -8.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7164   -8.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4219   -6.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8371   -5.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7076   -5.9241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3818   -5.2050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1273   -5.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7184   -4.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5129   -3.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7173   -3.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1273   -4.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3359   -4.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5691   -5.9409    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.3482   -8.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5125   -4.6743    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.7047   -8.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1561   -9.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5000   -9.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 19 26  1  0
 25 27  1  0
  4 13  2  0
 25 28  1  0
  1  2  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761651

   trans-rac-2-(7-chloro-5-(2-chlorophenyl)-1-(2-hydroxy-2-methylpropyl)-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: 436.34

Molecular Weight (Monoisotopic): 435.1004

AlogP: 4.30

#Rotatable Bonds: 5

Polar Surface Area: 77.84

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.94

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 0.53

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.73

Np Likeness Score: -0.08

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