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

ID: ALA1761660

PubChem CID: 54582326

Max Phase: Preclinical

Molecular Formula: C28H35ClN2O3

Molecular Weight: 483.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1[C@H]1CN(CC(=O)N2CCCCC2)C(=O)[C@H](CC(C)C)c2ccc(Cl)cc21

Standard InChI:  InChI=1S/C28H35ClN2O3/c1-19(2)15-24-21-12-11-20(29)16-23(21)25(22-9-5-6-10-26(22)34-3)17-31(28(24)33)18-27(32)30-13-7-4-8-14-30/h5-6,9-12,16,19,24-25H,4,7-8,13-15,17-18H2,1-3H3/t24-,25-/m1/s1

Standard InChI Key:  VMCQFERNKVBDRT-JWQCQUIFSA-N

Molfile:  

     RDKit          2D

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   -3.7669  -27.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5639  -25.9842    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4294  -28.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362  -24.7242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8215  -25.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474  -25.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 15 17  2  0
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  3 18  1  1
  8  9  2  0
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  5 12  1  6
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  4 13  2  0
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  1  2  1  0
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  1 14  1  0
  6  7  2  0
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  2  3  1  0
 15 16  1  0
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 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1761660

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

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: 483.05

Molecular Weight (Monoisotopic): 482.2336

AlogP: 5.46

#Rotatable Bonds: 6

Polar Surface Area: 49.85

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.92

CX LogD: 4.92

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.55

Np Likeness Score: -0.46

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