rac-3-(6-(cyclopropylmethyl)-7-methyl-6-azabicyclo[3.2.1]octan-1-yl)phenol hydrochloride

ID: ALA3251464

PubChem CID: 68145078

Max Phase: Preclinical

Molecular Formula: C18H26ClNO

Molecular Weight: 271.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1N(CC2CC2)C2CCCC1(c1cccc(O)c1)C2.Cl

Standard InChI:  InChI=1S/C18H25NO.ClH/c1-13-18(15-4-2-6-17(20)10-15)9-3-5-16(11-18)19(13)12-14-7-8-14;/h2,4,6,10,13-14,16,20H,3,5,7-9,11-12H2,1H3;1H

Standard InChI Key:  BLOXCOPNFWBEPK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   27.7392  -15.5185    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.1013  -15.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9672  -14.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4320  -14.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6421  -14.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1222  -15.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9706  -15.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4289  -14.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1005  -14.1309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8975  -14.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5004  -14.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7571  -14.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4111  -15.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8094  -15.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5505  -15.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6220  -13.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6354  -13.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3610  -13.7242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3293  -13.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8462  -14.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0401  -13.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  2  7  1  0
  7  3  1  0
  5  8  1  0
  2  9  1  0
  8  9  1  0
  5 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  9 16  1  0
  8 17  1  0
 12 18  1  0
 16 19  1  0
 20 19  1  0
 21 20  1  0
 19 21  1  0
M  END

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: 271.40

Molecular Weight (Monoisotopic): 271.1936

AlogP: 3.69

#Rotatable Bonds: 3

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: 10.48

CX LogP: 3.13

CX LogD: 1.14

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.91

Np Likeness Score: 0.64

References

1. Takeda M, Inoue H, Noguchi K, Honma Y, Kawamori M..  (1977)  Azabicycloalkanes as analgetics. 3. Structure-activity relationships of 1-phenyl-6-azabicyclo[3.2.1]octanes and absolute stereochemistry of (+)-1-(3-hydroxyphenyl)-6-methyl-6-azabicyclo[3.2.1]octane and its 7-endo-methyl derivative.,  20  (2): [PMID:401892] [10.1021/jm00212a007]

Source

Source(1):

• Scientific Literature