(1R,2S,3R,5R)-methyl 3-(4-ethynylphenyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylate

ID: ALA394158

PubChem CID: 44431739

Max Phase: Preclinical

Molecular Formula: C17H19NO2

Molecular Weight: 269.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1ccc([C@@H]2C[C@H]3CC[C@@H](N3)[C@H]2C(=O)OC)cc1

Standard InChI:  InChI=1S/C17H19NO2/c1-3-11-4-6-12(7-5-11)14-10-13-8-9-15(18-13)16(14)17(19)20-2/h1,4-7,13-16,18H,8-10H2,2H3/t13-,14+,15-,16+/m1/s1

Standard InChI Key:  TYFSSZYOVLRLQK-QXSJWSMHSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  1  0  0  0  0  0999 V2000
    9.2119   -9.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8556  -10.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5615   -9.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6672   -9.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8870   -8.4869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0746   -9.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8853   -9.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6190   -9.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9314  -11.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2548  -11.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3302  -12.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0801  -12.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7556  -12.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6769  -11.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8187   -9.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4993   -9.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8824   -8.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2434   -9.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7917   -8.5417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -9.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1570  -13.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2336  -14.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 10 11  1  0
  4  5  1  0
 11 12  2  0
  5  1  1  0
 12 13  1  0
  1  6  1  0
 13 14  2  0
 14  9  1  0
  6  2  1  0
  6 15  1  1
  4  7  1  0
 15 16  1  0
  1  8  1  0
 15 17  2  0
  7  8  1  0
 16 18  1  0
  1 19  1  6
  2  9  1  6
  4 20  1  6
  2  3  1  0
 12 21  1  0
  9 10  2  0
 21 22  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA394158

   (1R,2S,3R,5R)-methyl 3-(4-ethynylphenyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylate

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: 269.34

Molecular Weight (Monoisotopic): 269.1416

AlogP: 2.06

#Rotatable Bonds: 2

Polar Surface Area: 38.33

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.97

CX LogP: 2.28

CX LogD: -0.21

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: 0.75

References

1. Zeng F, Stehouwer JS, Jarkas N, Voll RJ, Williams L, Camp VM, Votaw JR, Owens MJ, Kilts CD, Nemeroff CB, Goodman MM..  (2007)  Synthesis and biological evaluation of 2beta,3alpha-(substituted phenyl)nortropanes as potential norepinephrine transporter imaging agents.,  17  (11): [PMID:17446069] [10.1016/j.bmcl.2007.03.056]

Source

Source(1):

• Scientific Literature