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

ID: ALA1761656

PubChem CID: 54581313

Max Phase: Preclinical

Molecular Formula: C24H28ClNO5

Molecular Weight: 445.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc([C@H]2CN(CC(=O)O)C(=O)[C@H](CC(C)C)c3ccc(Cl)cc32)c1OC

Standard InChI:  InChI=1S/C24H28ClNO5/c1-14(2)10-19-16-9-8-15(25)11-18(16)20(12-26(24(19)29)13-22(27)28)17-6-5-7-21(30-3)23(17)31-4/h5-9,11,14,19-20H,10,12-13H2,1-4H3,(H,27,28)/t19-,20-/m1/s1

Standard InChI Key:  AQYUGNGWEXBZGP-WOJBJXKFSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   21.0848  -14.0525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6788  -13.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8667  -13.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7289  -14.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9092  -15.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2231  -14.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2211  -13.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5194  -13.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8191  -13.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8250  -14.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5273  -14.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7171  -15.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2497  -15.4645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9553  -14.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3705  -13.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2410  -13.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9152  -12.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6606  -12.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2517  -11.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0462  -10.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2506  -10.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6606  -11.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8692  -12.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1024  -13.2575    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.8815  -16.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6894  -16.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2380  -15.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0458  -11.9909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6365  -11.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6353  -10.3915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4300  -10.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1  2  1  0
 28 29  1  0
  1 14  1  0
 20 30  1  0
  6  7  2  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761656

   trans-rac-2-(7-chloro-5-(2,3-dimethoxyphenyl)-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: 445.94

Molecular Weight (Monoisotopic): 445.1656

AlogP: 4.55

#Rotatable Bonds: 7

Polar Surface Area: 76.07

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.78

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 1.00

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.68

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