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

ID: ALA3114618

PubChem CID: 76325079

Max Phase: Preclinical

Molecular Formula: C21H23ClN2O2

Molecular Weight: 370.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1C[C@@H]1c1ccccc1)N1CCC(Oc2ccccc2Cl)CC1

Standard InChI:  InChI=1S/C21H23ClN2O2/c22-18-8-4-5-9-20(18)26-16-10-12-24(13-11-16)21(25)23-19-14-17(19)15-6-2-1-3-7-15/h1-9,16-17,19H,10-14H2,(H,23,25)/t17-,19+/m1/s1

Standard InChI Key:  WBQQANWTXAHQPL-MJGOQNOKSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   15.8793  -12.8793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5938  -12.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3082  -12.8793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5938  -11.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0227  -12.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8458  -12.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4333  -11.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5603  -12.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5557  -13.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2693  -14.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9848  -13.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9821  -12.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2679  -12.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1649  -12.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4526  -12.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4483  -13.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1627  -14.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8812  -13.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7324  -14.1087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0194  -13.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0280  -12.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3158  -12.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5989  -12.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5984  -13.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3111  -14.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7454  -12.4619    0.0000 Cl  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
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3114618

   4-(2-chlorophenoxy)-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: 370.88

Molecular Weight (Monoisotopic): 370.1448

AlogP: 4.45

#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: 3.53

CX LogD: 3.53

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.86

Np Likeness Score: -1.10

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