N-(2-((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)adamantane-1-carboxamide

ID: ALA4759505

PubChem CID: 150781593

Max Phase: Preclinical

Molecular Formula: C22H33NO

Molecular Weight: 327.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)[C@H]2CC=C(CCNC(=O)C34CC5CC(CC(C5)C3)C4)[C@@H]1C2

Standard InChI:  InChI=1S/C22H33NO/c1-21(2)18-4-3-17(19(21)10-18)5-6-23-20(24)22-11-14-7-15(12-22)9-16(8-14)13-22/h3,14-16,18-19H,4-13H2,1-2H3,(H,23,24)/t14?,15?,16?,18-,19-,22?/m0/s1

Standard InChI Key:  KBZMMMBGVMFVFL-XJPUKHNYSA-N

Molfile:  

 
     RDKit          2D

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   16.1746   -5.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7701   -4.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3612   -5.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8846   -5.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5238   -5.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6814   -5.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2285   -5.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4352   -5.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9775   -5.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6787   -4.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2342   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5194   -4.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9833   -4.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2290   -3.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9382   -2.8887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5146   -2.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6485   -3.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3577   -2.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0670   -3.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0653   -4.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4790   -4.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4779   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7682   -2.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7619   -3.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3708   -4.5386    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1785   -4.5285    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  7  1  0
  6  8  1  0
  7  9  1  0
  8  9  1  0
 10 11  1  0
  6 10  1  0
  5 12  1  0
  9 13  1  0
 13 11  1  0
 11 12  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 23  2  0
 20  2  1  0
  2 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 21  1  0
 20 25  1  1
 21 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4759505

   ---

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: 327.51

Molecular Weight (Monoisotopic): 327.2562

AlogP: 4.70

#Rotatable Bonds: 4

Polar Surface Area: 29.10

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.48

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: 0.35

References

1. Suslov, Evgenii V., Mozhaytsev, Evgenii S., Korchagina, Dina V., Bormotov, Nikolay I., Yarovaya, Olga I., Volcho, Konstantin P., Serova, Olga A., Agafonov, Alexander P., Maksyutov, Rinat A., Shishkina, Larisa N., Salakhutdinov, Nariman F..  (2020)  New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections,  11  (10): [PMID:33479623] [10.1039/d0md00108b]

Source

Source(1):

• Scientific Literature