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

ID: ALA3114611

PubChem CID: 76325076

Max Phase: Preclinical

Molecular Formula: C21H24N2O2

Molecular Weight: 336.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1C[C@@H]1c1ccccc1)N1CCC(Oc2ccccc2)CC1

Standard InChI:  InChI=1S/C21H24N2O2/c24-21(22-20-15-19(20)16-7-3-1-4-8-16)23-13-11-18(12-14-23)25-17-9-5-2-6-10-17/h1-10,18-20H,11-15H2,(H,22,24)/t19-,20+/m1/s1

Standard InChI Key:  SAKQSHLUPVUJDT-UXHICEINSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   19.7433   -3.4379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4577   -3.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1723   -3.4379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4577   -2.2002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8868   -3.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7100   -3.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2975   -2.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4244   -3.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4199   -4.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1337   -4.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8492   -4.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8465   -3.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1322   -3.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0289   -3.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3166   -3.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3122   -4.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0266   -4.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7453   -4.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5961   -4.6673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8832   -4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8918   -3.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1796   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4626   -3.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4621   -4.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1748   -4.6632    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
M  END

Alternative Forms

1. Parent:

   

   ALA3114611

   4-Phenoxy-N-[(1s,2r)-2-Phenylcyclopropyl]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: 336.44

Molecular Weight (Monoisotopic): 336.1838

AlogP: 3.80

#Rotatable Bonds: 4

Polar Surface Area: 41.57

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.92

CX LogD: 2.92

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.92

Np Likeness Score: -0.88

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