N-(2-Aminoethyl)-2-((R,R)-dispiro[adamantane-2,3'-[1,2,4]trioxolane-5',1''-cyclohexan]-3''-yl)acetamide

ID: ALA4104318

PubChem CID: 137390456

Max Phase: Preclinical

Molecular Formula: C20H32N2O4

Molecular Weight: 364.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCNC(=O)C[C@@H]1CCC[C@]2(C1)OOC1(O2)C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C20H32N2O4/c21-4-5-22-18(23)11-13-2-1-3-19(12-13)24-20(26-25-19)16-7-14-6-15(9-16)10-17(20)8-14/h13-17H,1-12,21H2,(H,22,23)/t13-,14?,15?,16?,17?,19+,20-/m0/s1

Standard InChI Key:  DPCWAYIKUFJTMR-UEQYWLTKSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   21.9444   -7.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8141   -7.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2243   -7.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0444   -7.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4607   -7.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0507   -6.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2243   -6.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5673   -7.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3666   -7.7638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2954   -6.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5234   -6.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4508   -8.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0947   -8.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2545   -8.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8049   -8.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0146   -9.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5561   -8.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2518   -7.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8107   -7.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0902   -7.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4679   -5.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2965   -5.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7138   -4.9311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7077   -6.3662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5363   -6.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5303   -7.8048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  9  1  0
  9  2  1  0
  2 10  1  1
 10 11  1  0
  8 11  1  1
 12 13  1  0
 12 14  1  0
 13 15  1  0
 14 16  1  0
 15 17  1  0
 16 17  1  0
 18 19  1  0
 14 18  1  0
 13 20  1  0
 17  8  1  0
  8 19  1  0
 19 20  1  0
  6 21  1  6
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25  1  1  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104318

   ---

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: 364.49

Molecular Weight (Monoisotopic): 364.2362

AlogP: 2.47

#Rotatable Bonds: 4

Polar Surface Area: 82.81

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.16

CX LogP: 2.41

CX LogD: 0.66

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: 0.85

References

1. Blank BR, Gut J, Rosenthal PJ, Renslo AR..  (2017)  Enantioselective Synthesis and in Vivo Evaluation of Regioisomeric Analogues of the Antimalarial Arterolane.,  60  (14): [PMID:28692297] [10.1021/acs.jmedchem.7b00699]

Source

Source(1):

• Scientific Literature