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

ID: ALA1761661

PubChem CID: 54581314

Max Phase: Preclinical

Molecular Formula: C29H35ClN2O5

Molecular Weight: 527.06

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1[C@H]1CN(CC(=O)N2CCC(C(=O)O)CC2)C(=O)[C@H](CC(C)C)c2ccc(Cl)cc21

Standard InChI:  InChI=1S/C29H35ClN2O5/c1-18(2)14-24-21-9-8-20(30)15-23(21)25(22-6-4-5-7-26(22)37-3)16-32(28(24)34)17-27(33)31-12-10-19(11-13-31)29(35)36/h4-9,15,18-19,24-25H,10-14,16-17H2,1-3H3,(H,35,36)/t24-,25-/m1/s1

Standard InChI Key:  UIDVDWBJUGYMJC-JWQCQUIFSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
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    5.3109  -25.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5034  -25.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607  -26.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456  -26.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635  -26.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8615  -25.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638  -25.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4675  -25.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3546  -27.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8785  -27.3909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5801  -25.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9929  -25.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8862  -23.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8908  -22.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042  -23.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116  -24.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7548  -25.1965    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5238  -28.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3328  -28.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8840  -27.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6758  -23.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3045  -25.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1664  -25.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5833  -25.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1318  -24.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2634  -24.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4492  -25.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9011  -25.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8668  -24.3561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2631  -23.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 16 29  1  0
  1  2  1  0
  1 14  1  0
  6  7  2  0
 14 15  1  0
  2  3  1  0
 16 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 15 16  1  0
 31 34  1  0
  7  8  1  0
 15 17  2  0
 34 35  1  0
 34 36  2  0
  1  4  1  0
 28 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761661

   trans-rac-1-(2-(7-chloro-1-isobutyl-5-(2-methoxyphenyl)-2-oxo-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)acetyl)piperidine-4-carboxylic 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: 527.06

Molecular Weight (Monoisotopic): 526.2234

AlogP: 4.78

#Rotatable Bonds: 7

Polar Surface Area: 87.15

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.04

CX Basic pKa: ┄

CX LogP: 4.15

CX LogD: 1.01

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.56

Np Likeness Score: -0.44

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