(E)-N-(2-(Adamantan-2-yloxy)ethyl)-3,7-dimethylocta-2,6-dien-1-amine

ID: ALA3261880

PubChem CID: 90655951

Max Phase: Preclinical

Molecular Formula: C22H37NO

Molecular Weight: 331.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/CNCCOC1C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C22H37NO/c1-16(2)5-4-6-17(3)7-8-23-9-10-24-22-20-12-18-11-19(14-20)15-21(22)13-18/h5,7,18-23H,4,6,8-15H2,1-3H3/b17-7+

Standard InChI Key:  WQFPRNRSNLQWLT-REZTVBANSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   15.9302   -2.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5714   -1.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7304   -2.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2786   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4873   -2.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0265   -1.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7278   -1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2844   -0.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5670   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0365   -1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7248   -0.5739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4628   -0.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1512   -0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8892   -0.8568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5775   -0.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3155   -0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0039   -0.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7419   -0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9542    0.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4302   -0.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1682   -0.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8566   -0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5946   -0.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8069    0.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3261880

   (2E)-N-[2-(2-adamantyloxy)ethyl]-3,7-dimethyl-octa-2,6-dien-1-amine

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: 331.54

Molecular Weight (Monoisotopic): 331.2875

AlogP: 5.11

#Rotatable Bonds: 9

Polar Surface Area: 21.26

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.10

CX LogP: 4.96

CX LogD: 3.26

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.47

Np Likeness Score: 0.99

References

1. Li K, Schurig-Briccio LA, Feng X, Upadhyay A, Pujari V, Lechartier B, Fontes FL, Yang H, Rao G, Zhu W, Gulati A, No JH, Cintra G, Bogue S, Liu YL, Molohon K, Orlean P, Mitchell DA, Freitas-Junior L, Ren F, Sun H, Jiang T, Li Y, Guo RT, Cole ST, Gennis RB, Crick DC, Oldfield E..  (2014)  Multitarget drug discovery for tuberculosis and other infectious diseases.,  57  (7): [PMID:24568559] [10.1021/jm500131s]

Source

Source(1):

• Scientific Literature