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

ID: ALA3114603

PubChem CID: 76325075

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(Oc2ccc(-c3ccccc3)cc2)CC1

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

Standard InChI Key:  UOYCWQZNXUQGJP-FTJBHMTQSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   30.2812  -30.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9957  -30.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7103  -30.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9957  -29.4229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4248  -30.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2479  -30.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8354  -29.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9624  -30.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9579  -31.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6715  -31.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3870  -31.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3844  -30.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6701  -30.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5668  -30.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8544  -30.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8502  -31.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5646  -31.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2832  -31.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1342  -31.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4212  -31.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4298  -30.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7176  -30.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0005  -30.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0000  -31.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7128  -31.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2870  -30.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2939  -29.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5812  -28.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8647  -29.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8653  -30.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5786  -30.6448    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
 23 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:

   

   ALA3114603

   N-[(1S,2R)-2-phenylcyclopropyl]-4-(4-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: -0.75

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