cis-N-benzyl-N-methyl-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-3'-amine

ID: ALA4781486

PubChem CID: 162664817

Max Phase: Preclinical

Molecular Formula: C22H27NO

Molecular Weight: 321.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(Cc1ccccc1)[C@H]1CCC[C@]2(C1)OCCc1ccccc12

Standard InChI:  InChI=1S/C22H27NO/c1-23(17-18-8-3-2-4-9-18)20-11-7-14-22(16-20)21-12-6-5-10-19(21)13-15-24-22/h2-6,8-10,12,20H,7,11,13-17H2,1H3/t20-,22+/m0/s1

Standard InChI Key:  MUHCISPOTDLLAG-RBBKRZOGSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   34.0950  -10.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3810  -10.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6720  -10.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6708  -11.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3849  -11.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1000  -11.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0950   -9.6825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5097   -9.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8044   -9.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5097  -10.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8050  -10.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8016  -11.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5021  -12.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2117  -11.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2117  -10.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3851  -12.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6775  -12.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9697  -12.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9724  -11.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2654  -11.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5568  -11.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5597  -12.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2673  -12.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0929  -12.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  1
  7  9  1  0
  1 11  1  0
 10  8  1  0
  8  9  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
  5 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 16 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781486

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 321.46

Molecular Weight (Monoisotopic): 321.2093

AlogP: 4.53

#Rotatable Bonds: 3

Polar Surface Area: 12.47

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.73

CX LogP: 4.59

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: -0.27

References

1. Kronenberg, Elisabeth, Weber, Frauke, Schepmann, Dirk, Wunsch, Bernhard.  (2021)  Synthesis and sigma receptor affinity of spiro[[2]benzopyran-1,1-cyclohexanes] with an exocyclic amino moiety in the 3-position,  12  (2): [PMID:34046612] [10.1039/d0md00307g]

Source

Source(1):

• Scientific Literature