(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 3-(dibutylamino)propanoate

ID: ALA4281725

PubChem CID: 145982211

Max Phase: Preclinical

Molecular Formula: C21H39NO2

Molecular Weight: 337.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN(CCCC)CCC(=O)O[C@@H]1C[C@@H]2CC[C@@]1(C)C2(C)C

Standard InChI:  InChI=1S/C21H39NO2/c1-6-8-13-22(14-9-7-2)15-11-19(23)24-18-16-17-10-12-21(18,5)20(17,3)4/h17-18H,6-16H2,1-5H3/t17-,18+,21+/m0/s1

Standard InChI Key:  LULZKQIRLWQMTP-WAOWUJCRSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   22.1302  -25.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4327  -26.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1348  -26.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3431  -25.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3431  -26.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0401  -27.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7330  -26.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7330  -25.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0401  -25.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6484  -27.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0324  -27.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0324  -24.7015    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.9406  -26.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2330  -27.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9403  -25.8955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5251  -26.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8175  -27.1219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1097  -26.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8178  -27.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4021  -27.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6943  -26.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9867  -27.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1102  -28.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4024  -27.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6948  -28.3482    0.0000 C   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  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6  2  1  0
  9  2  1  0
  5 10  1  6
  6 11  1  1
  9 12  1  1
 10 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4281725

   ---

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: 337.55

Molecular Weight (Monoisotopic): 337.2981

AlogP: 5.04

#Rotatable Bonds: 10

Polar Surface Area: 29.54

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.10

CX LogP: 5.21

CX LogD: 2.57

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: 0.68

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]

Source

Source(1):

• Scientific Literature