N-[(1SR,2RS)-2-Phenylcyclopropyl]-4-(pyridin-4-yloxy)piperidine-1-carboxamide

ID: ALA3114614

PubChem CID: 76332320

Max Phase: Preclinical

Molecular Formula: C20H23N3O2

Molecular Weight: 337.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1C[C@@H]1c1ccccc1)N1CCC(Oc2ccncc2)CC1

Standard InChI:  InChI=1S/C20H23N3O2/c24-20(22-19-14-18(19)15-4-2-1-3-5-15)23-12-8-17(9-13-23)25-16-6-10-21-11-7-16/h1-7,10-11,17-19H,8-9,12-14H2,(H,22,24)/t18-,19+/m1/s1

Standard InChI Key:  SMTNPXAWRZTFQE-MOPGFXCFSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   17.4695   -7.7156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1842   -7.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8990   -7.7156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1842   -6.4776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6137   -7.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4371   -7.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0244   -6.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1519   -7.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1473   -8.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8613   -8.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5770   -8.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5743   -7.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8598   -7.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7549   -7.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0423   -7.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0380   -8.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7526   -8.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4715   -8.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3217   -8.9455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6084   -8.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6170   -7.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9047   -7.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1874   -7.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1869   -8.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8999   -8.9414    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:

   

   ALA3114614

   N-[(1S,2R)-2-phenylcyclopropyl]-4-pyridin-4-yloxypiperidine-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: 337.42

Molecular Weight (Monoisotopic): 337.1790

AlogP: 3.19

#Rotatable Bonds: 4

Polar Surface Area: 54.46

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.47

CX LogP: 1.71

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.93

Np Likeness Score: -1.02

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