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

ID: ALA3114615

PubChem CID: 76332321

Max Phase: Preclinical

Molecular Formula: C19H22N4O2

Molecular Weight: 338.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1C[C@@H]1c1ccccc1)N1CCC(Oc2ncccn2)CC1

Standard InChI:  InChI=1S/C19H22N4O2/c24-19(22-17-13-16(17)14-5-2-1-3-6-14)23-11-7-15(8-12-23)25-18-20-9-4-10-21-18/h1-6,9-10,15-17H,7-8,11-13H2,(H,22,24)/t16-,17+/m1/s1

Standard InChI Key:  NYYOUJRVKSVQEF-SJORKVTESA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   17.4627   -7.7126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1771   -7.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8916   -7.7126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1771   -6.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6061   -7.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4291   -7.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0166   -6.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1436   -7.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1390   -8.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8527   -8.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5682   -8.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5655   -7.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8512   -7.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7483   -7.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0360   -7.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0317   -8.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7460   -8.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4647   -8.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157   -8.9420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6027   -8.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6113   -7.7025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8992   -7.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1822   -7.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1817   -8.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8944   -8.9379    0.0000 N   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:

   

   ALA3114615

   N-[(1S,2R)-2-phenylcyclopropyl]-4-pyrimidin-2-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: 338.41

Molecular Weight (Monoisotopic): 338.1743

AlogP: 2.59

#Rotatable Bonds: 4

Polar Surface Area: 67.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.89

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.93

Np Likeness Score: -1.18

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