trans-N-(Cyclohexylmethyl)-3-methoxy-3H-spiro[[2]benzofuran-1,1'-cyclohexan]-4'-amine

ID: ALA4483557

Max Phase: Preclinical

Molecular Formula: C21H31NO2

Molecular Weight: 329.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC1O[C@]2(CC[C@H](NCC3CCCCC3)CC2)c2ccccc21

Standard InChI:  InChI=1S/C21H31NO2/c1-23-20-18-9-5-6-10-19(18)21(24-20)13-11-17(12-14-21)22-15-16-7-3-2-4-8-16/h5-6,9-10,16-17,20,22H,2-4,7-8,11-15H2,1H3/t17-,20?,21-

Standard InChI Key:  XDSZKZOLLACLGI-WQUIYQLNSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    4.7215  -26.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396  -27.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3479  -27.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381  -28.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7200  -27.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5118  -26.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244  -25.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5233  -26.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2313  -26.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2296  -24.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382  -25.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430  -26.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004  -25.7766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7153  -25.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3457  -28.8128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1340  -29.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7147  -28.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5021  -28.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0816  -28.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8780  -27.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0893  -27.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5043  -27.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9632  -24.3386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7615  -24.1640    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
 12  1  1  0
  1 13  1  1
 13 14  1  0
 14 11  1  0
  4 15  1  6
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 14 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483557

   ---

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: 329.48

Molecular Weight (Monoisotopic): 329.2355

AlogP: 4.67

#Rotatable Bonds: 4

Polar Surface Area: 30.49

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.10

CX LogP: 4.66

CX LogD: 1.54

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.87

Np Likeness Score: 0.50

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