8-(tetrahydrofuran-3-carbonyl)-N-(4-(trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decane-2-carboxamide

ID: ALA2436582

PubChem CID: 72376216

Max Phase: Preclinical

Molecular Formula: C21H26F3N3O4

Molecular Weight: 441.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(OC(F)(F)F)cc1)N1CCC2(CCN(C(=O)C3CCOC3)CC2)C1

Standard InChI:  InChI=1S/C21H26F3N3O4/c22-21(23,24)31-17-3-1-16(2-4-17)25-19(29)27-11-8-20(14-27)6-9-26(10-7-20)18(28)15-5-12-30-13-15/h1-4,15H,5-14H2,(H,25,29)

Standard InChI Key:  LPUPTEXTLYVCLC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   12.3756  -11.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1583  -12.2052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1775  -13.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4062  -13.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9102  -12.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668  -10.4423    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5269  -13.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2373  -13.7279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061  -13.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022  -13.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4108  -14.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4007  -12.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9909  -13.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743  -12.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1305  -14.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1837  -14.0037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0045  -14.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6872  -10.8534    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6921  -13.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5460  -13.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622  -10.8553    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7700  -14.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6893  -12.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8165  -13.7279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3276  -14.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5269  -12.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7721  -13.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1103  -12.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513  -13.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732  -11.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9533  -14.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
 24  7  1  0
 20 29  1  0
 23 14  1  0
 30 18  1  0
 20 13  1  0
 16 17  1  0
 16 27  1  0
 30  6  1  0
 27 29  1  0
 17  4  1  0
  7  8  1  0
 12 23  2  0
 15 20  1  0
 14 30  1  0
 17 11  2  0
 22 16  1  0
 19 10  2  0
  8 25  1  0
 25 15  1  0
  7 26  2  0
 28 12  1  0
 31 22  1  0
 23 19  1  0
 30 21  1  0
 10  9  1  0
 13  8  1  0
 24  9  1  0
  9 28  2  0
 20 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2436582

   8-(oxolane-3-carbonyl)-N-[4-(trifluoromethoxy)phenyl]-2,8-diazaspiro[4.5]decane-2-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: 441.45

Molecular Weight (Monoisotopic): 441.1875

AlogP: 3.47

#Rotatable Bonds: 3

Polar Surface Area: 71.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.75

CX Basic pKa: ┄

CX LogP: 2.51

CX LogD: 2.51

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.78

Np Likeness Score: -1.14

References

1. Kato Y, Fuchi N, Saburi H, Nishimura Y, Watanabe A, Yagi M, Nakadera Y, Higashi E, Yamada M, Aoki T..  (2013)  Discovery of 2,8-diazaspiro[4.5]decane-based trisubstituted urea derivatives as highly potent soluble epoxide hydrolase inhibitors and orally active drug candidates for treating hypertension.,  23  (21): [PMID:24035338] [10.1016/j.bmcl.2013.08.054]

Source

Source(1):

• Scientific Literature