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

ID: ALA4576927

Max Phase: Preclinical

Molecular Formula: C23H35NO2

Molecular Weight: 357.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC1Cc2ccccc2[C@]2(CC[C@@H](N(C)CC3CCCCC3)CC2)O1

Standard InChI:  InChI=1S/C23H35NO2/c1-24(17-18-8-4-3-5-9-18)20-12-14-23(15-13-20)21-11-7-6-10-19(21)16-22(25-2)26-23/h6-7,10-11,18,20,22H,3-5,8-9,12-17H2,1-2H3/t20-,22?,23-

Standard InChI Key:  MBRMOGQHSBUGKH-FXCIWXGGSA-N

Molfile:  

 
     RDKit          2D

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   28.8456  -18.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1271  -18.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4135  -18.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4123  -19.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1309  -20.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8506  -19.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8456  -18.0093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2693  -18.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5595  -17.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2693  -18.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2616  -20.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9757  -20.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9757  -19.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5600  -19.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5689  -20.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6960  -20.0786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9796  -19.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2633  -20.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5509  -19.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8366  -20.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8324  -20.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5485  -21.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2648  -20.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5605  -16.7716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2733  -16.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6959  -20.9010    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
 10  8  1  0
  8  9  1  0
 10 14  2  0
 15 11  2  0
 11 12  1  0
 12 13  2  0
 13 10  1  0
 14  1  1  0
 14 15  1  0
  4 16  1  6
 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
  9 24  1  0
 24 25  1  0
 16 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4576927

   ---

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: 357.54

Molecular Weight (Monoisotopic): 357.2668

AlogP: 4.88

#Rotatable Bonds: 4

Polar Surface Area: 21.70

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.03

CX LogP: 5.10

CX LogD: 1.84

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: 0.35

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