(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-(piperidin-1-yl)acetate

ID: ALA4289184

PubChem CID: 92325485

Max Phase: Preclinical

Molecular Formula: C17H29NO2

Molecular Weight: 279.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)[C@H]2CC[C@]1(C)[C@H](OC(=O)CN1CCCCC1)C2

Standard InChI:  InChI=1S/C17H29NO2/c1-16(2)13-7-8-17(16,3)14(11-13)20-15(19)12-18-9-5-4-6-10-18/h13-14H,4-12H2,1-3H3/t13-,14+,17+/m0/s1

Standard InChI Key:  VCLQKOONPZMQKL-JJRVBVJISA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   10.7390   -7.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4494   -7.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6330   -7.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6330   -7.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3382   -8.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0435   -7.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0435   -7.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3382   -6.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1545   -9.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9258   -8.3587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5273   -7.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1313   -5.9286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2175   -7.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5104   -8.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2164   -7.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8021   -7.9532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8034   -7.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0992   -6.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3896   -7.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3889   -7.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0976   -8.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  3  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  1  1  0
  5  1  1  0
  5  9  1  1
  4 10  1  6
  1 11  1  0
  8 12  1  1
 10 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4289184

   [(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-piperidin-1-ylacetate

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: 279.42

Molecular Weight (Monoisotopic): 279.2198

AlogP: 3.23

#Rotatable Bonds: 3

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.63

CX LogP: 3.17

CX LogD: 3.10

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.74

Np Likeness Score: 0.63

References

1. Kononova AA, Sokolova AS, Cheresiz SV, Yarovaya OI, Nikitina RA, Chepurnov AA, Pokrovsky AG, Salakhutdinov NF..  (2017)  N-Heterocyclic borneol derivatives as inhibitors of Marburg virus glycoprotein-mediated VSIV pseudotype entry.,  8  (12): [PMID:30108738] [10.1039/C7MD00424A]

2. Sokolova AS, Yarovaya OI, Semenova MD, Shtro AA, Orshanskaya IR, Zarubaev VV, Salakhutdinov NF..  (2017)  Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus.,  8  (5): [PMID:30108810] [10.1039/C6MD00657D]

3. Sokolova AS,Yarovaya OI,Zybkina AV,Mordvinova ED,Shcherbakova NS,Zaykovskaya AV,Baev DS,Tolstikova TG,Shcherbakov DN,Pyankov OV,Maksyutov RA,Salakhutdinov NF.  (2020)  Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process.,  207  [PMID:32905862] [10.1016/j.ejmech.2020.112726]

Source

Source(1):

• Scientific Literature