cis-N-(Cyclohexylmethyl)-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

ID: ALA4557149

Max Phase: Preclinical

Molecular Formula: C21H31NO

Molecular Weight: 313.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1ccc2c(c1)CCO[C@]21CC[C@@H](NCC2CCCCC2)CC1

Standard InChI:  InChI=1S/C21H31NO/c1-2-6-17(7-3-1)16-22-19-10-13-21(14-11-19)20-9-5-4-8-18(20)12-15-23-21/h4-5,8-9,17,19,22H,1-3,6-7,10-16H2/t19-,21+

Standard InChI Key:  AQZKAHGFUOVNTK-TYKWCNGQSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   12.1836   -3.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4737   -3.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4691   -4.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1726   -4.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8825   -4.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8888   -3.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0649   -1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0637   -2.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7718   -3.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7700   -1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4786   -1.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4774   -2.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9034   -2.6891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9046   -1.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1899   -1.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1668   -5.5437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8716   -5.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5822   -5.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2823   -5.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9908   -5.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0008   -4.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2961   -4.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5815   -4.7398    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
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 11 15  1  0
 12  1  1  0
  1 13  1  1
 13 14  1  0
 14 15  1  0
  4 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557149

   ---

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: 313.49

Molecular Weight (Monoisotopic): 313.2406

AlogP: 4.57

#Rotatable Bonds: 3

Polar Surface Area: 21.26

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.10

CX LogP: 4.67

CX LogD: 1.55

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.88

Np Likeness Score: 0.07

References

1. Kronenberg E, Weber F, Brune S, Schepmann D, Almansa C, Friedland K, Laurini E, Pricl S, Wünsch B..  (2019)  Synthesis and Structure-Affinity Relationships of Spirocyclic Benzopyrans with Exocyclic Amino Moiety.,  62  (8): [PMID:30939014] [10.1021/acs.jmedchem.9b00449]

Source

Source(1):

• Scientific Literature