{2-[(9R)-9-(Pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]ethyl}-(thiophen-2-ylmethyl)amine

ID: ALA2443278

PubChem CID: 72712370

Max Phase: Preclinical

Molecular Formula: C21H28N2OS

Molecular Weight: 356.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc([C@]2(CCNCc3cccs3)CCOC3(CCCC3)C2)nc1

Standard InChI:  InChI=1S/C21H28N2OS/c1-4-12-23-19(7-1)20(10-13-22-16-18-6-5-15-25-18)11-14-24-21(17-20)8-2-3-9-21/h1,4-7,12,15,22H,2-3,8-11,13-14,16-17H2/t20-/m1/s1

Standard InChI Key:  PJLIHYXPEOMIMJ-HXUWFJFHSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   13.9005  -11.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4333  -14.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4296  -12.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8418  -12.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9211  -15.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6668  -12.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1420  -13.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1824  -10.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7213  -13.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0129  -12.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9279  -13.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1378  -14.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4282  -11.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1887  -12.0149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3124  -10.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7703  -11.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1453  -13.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0122  -10.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4095  -14.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7213  -13.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0772  -11.2897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1270  -10.4845    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.2986   -9.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5861   -9.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9743   -9.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5 19  1  0
  8 16  1  0
  3 17  1  0
  4  6  1  0
  3 10  1  1
  7 12  1  0
  1 15  1  0
 19 11  1  0
  9 20  1  0
  7 17  1  0
 13 18  1  0
 16 14  2  0
 11  7  1  0
  2  7  1  0
 18  8  2  0
  3  4  1  0
 12  5  1  0
  3  9  1  0
 10 13  2  0
 14 10  1  0
 21  1  1  0
 20  2  1  0
  6 21  1  0
 15 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2443278

   2-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]-N-(thiophen-2-ylmethyl)ethanamine

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: 356.54

Molecular Weight (Monoisotopic): 356.1922

AlogP: 4.68

#Rotatable Bonds: 6

Polar Surface Area: 34.15

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.58

CX LogP: 4.11

CX LogD: 1.97

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -1.01

References

1. Chen XT, Pitis P, Liu G, Yuan C, Gotchev D, Cowan CL, Rominger DH, Koblish M, Dewire SM, Crombie AL, Violin JD, Yamashita DS..  (2013)  Structure-activity relationships and discovery of a G protein biased μ opioid receptor ligand, [(3-methoxythiophen-2-yl)methyl]({2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro-[4.5]decan-9-yl]ethyl})amine (TRV130), for the treatment of acute severe pain.,  56  (20): [PMID:24063433] [10.1021/jm4010829]

Source

Source(1):

• Scientific Literature