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

ID: ALA4287196

PubChem CID: 145992466

Max Phase: Preclinical

Molecular Formula: C18H32N2O2

Molecular Weight: 308.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCN(CC(=O)O[C@@H]2C[C@@H]3CC[C@@]2(C)C3(C)C)CC1

Standard InChI:  InChI=1S/C18H32N2O2/c1-5-19-8-10-20(11-9-19)13-16(21)22-15-12-14-6-7-18(15,4)17(14,2)3/h14-15H,5-13H2,1-4H3/t14-,15+,18+/m0/s1

Standard InChI Key:  CPLRYHNVPKEJRJ-HDMKZQKVSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    9.4720   -8.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1823   -8.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3659   -7.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3659   -8.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0712   -9.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7765   -8.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7765   -7.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0712   -7.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875   -9.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6588   -9.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2603   -7.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8642   -6.6426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9505   -8.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2434   -9.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9493   -7.8479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5351   -8.6672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5363   -7.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321   -7.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226   -7.8522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1218   -8.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305   -9.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4158   -7.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4177   -6.6247    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
 19 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4287196

   ---

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: 308.47

Molecular Weight (Monoisotopic): 308.2464

AlogP: 2.38

#Rotatable Bonds: 4

Polar Surface Area: 32.78

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.65

CX LogP: 2.53

CX LogD: 2.08

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: 0.38

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