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

ID: ALA1761655

PubChem CID: 54582324

Max Phase: Preclinical

Molecular Formula: C23H26ClNO4

Molecular Weight: 415.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1[C@H]1CN(CC(=O)O)C(=O)[C@H](CC(C)C)c2ccc(Cl)cc21

Standard InChI:  InChI=1S/C23H26ClNO4/c1-14(2)10-19-16-9-8-15(24)11-18(16)20(12-25(23(19)28)13-22(26)27)17-6-4-5-7-21(17)29-3/h4-9,11,14,19-20H,10,12-13H2,1-3H3,(H,26,27)/t19-,20-/m1/s1

Standard InChI Key:  YBPYETHENAODPQ-WOJBJXKFSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   13.1714  -13.6808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7654  -12.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9534  -12.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8155  -14.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9959  -14.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3098  -14.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3078  -13.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6062  -12.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9059  -13.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9118  -14.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6141  -14.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8038  -15.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3363  -15.0927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0418  -13.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4570  -12.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3274  -12.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0017  -12.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7473  -11.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3384  -11.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1329  -10.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3373  -10.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7474  -10.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9559  -11.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1893  -12.8858    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.9682  -15.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7762  -16.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3248  -15.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1324  -11.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7231  -11.0434    0.0000 C   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
 25 26  1  0
 25 27  1  0
  4 13  2  0
 19 28  1  0
  1  2  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761655

   trans-rac-2-(5-(2-methoxyphenyl)-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: 415.92

Molecular Weight (Monoisotopic): 415.1550

AlogP: 4.54

#Rotatable Bonds: 6

Polar Surface Area: 66.84

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: ┄

CX LogP: 4.43

CX LogD: 1.26

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.75

Np Likeness Score: 0.00

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