4-(Biphenyl-3-yloxy)-N-[(1SR,2RS)-2-phenylcyclopropyl]piperidine-1-carboxamide

ID: ALA3114602

PubChem CID: 76325074

Max Phase: Preclinical

Molecular Formula: C27H28N2O2

Molecular Weight: 412.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1C[C@@H]1c1ccccc1)N1CCC(Oc2cccc(-c3ccccc3)c2)CC1

Standard InChI:  InChI=1S/C27H28N2O2/c30-27(28-26-19-25(26)21-10-5-2-6-11-21)29-16-14-23(15-17-29)31-24-13-7-12-22(18-24)20-8-3-1-4-9-20/h1-13,18,23,25-26H,14-17,19H2,(H,28,30)/t25-,26+/m1/s1

Standard InChI Key:  PMKHFAXZSOGNAS-FTJBHMTQSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   17.7134  -29.9225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4280  -29.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1425  -29.9225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4280  -28.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8570  -29.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6802  -29.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2676  -28.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3947  -29.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3900  -30.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1037  -31.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8192  -30.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8166  -29.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1023  -29.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9991  -29.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2867  -29.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2825  -30.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9968  -31.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7154  -30.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5664  -31.1520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8535  -30.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8620  -29.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1499  -29.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4329  -29.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4324  -30.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1451  -31.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1534  -28.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8699  -28.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8738  -27.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1605  -27.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4419  -27.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4415  -28.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  5  3  1  1
  6  5  1  0
  7  6  1  0
  5  7  1  0
  6  8  1  6
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  1 14  1  0
  1 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3114602

   N-[(1S,2R)-2-phenylcyclopropyl]-4-(3-phenylphenoxy)piperidine-1-carboxamide

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: 412.53

Molecular Weight (Monoisotopic): 412.2151

AlogP: 5.46

#Rotatable Bonds: 5

Polar Surface Area: 41.57

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.57

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -0.81

References

1. Takai K, Nakajima T, Takanashi Y, Sone T, Nariai T, Chiyo N, Nakatani S, Ishikawa C, Yamaguchi N, Fujita K, Yamada K..  (2014)  Structure-based optimization of cyclopropyl urea derivatives as potent soluble epoxide hydrolase inhibitors for potential decrease of renal injury without hypotensive action.,  22  (5): [PMID:24530032] [10.1016/j.bmc.2014.01.040]

Source

Source(1):

• Scientific Literature