3,3'-(4-isopropyl-1,2-phenylene)bis(oxy)bis(1-(isopropylamino)propan-2-ol)dihydrochloride

ID: ALA3272438

PubChem CID: 90677518

Max Phase: Preclinical

Molecular Formula: C21H39ClN2O4

Molecular Weight: 382.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)NCC(O)COc1ccc(C(C)C)cc1OCC(O)CNC(C)C.Cl

Standard InChI:  InChI=1S/C21H38N2O4.ClH/c1-14(2)17-7-8-20(26-12-18(24)10-22-15(3)4)21(9-17)27-13-19(25)11-23-16(5)6;/h7-9,14-16,18-19,22-25H,10-13H2,1-6H3;1H

Standard InChI Key:  KDTMCXXFIVOBOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
   33.0079  -11.0818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.3646   -9.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3635  -10.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0782  -10.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7947  -10.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7919   -9.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0765   -9.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5099  -10.8422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5047   -9.1851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2208   -9.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9337   -9.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6497   -9.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9306   -8.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2236  -10.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9388  -10.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9401  -11.6648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6528  -10.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3626   -9.1743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3728  -10.8171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3841  -11.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1042  -12.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6754  -12.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0786   -9.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7915   -9.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0817  -10.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6487  -10.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9346  -10.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6480  -11.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  5  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  1  0
 12 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 23 25  1  0
  3 26  1  0
 26 27  1  0
 26 28  1  0
M  END

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: 382.55

Molecular Weight (Monoisotopic): 382.2832

AlogP: 2.29

#Rotatable Bonds: 13

Polar Surface Area: 82.98

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.79

CX Basic pKa: 9.97

CX LogP: 2.46

CX LogD: -1.99

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -0.24

References

1. Zaagsma J, Nauta WT..  (1977)  Beta-adrenoceptor studies. 2. Effects of alkyl substitution on beta-adrenoceptor blocking, antiarrhythmic, and local anesthetic activities of 1,1'-(o-phenylenedioxy)bis(3-isopropylamino-2-propanol).,  20  (4): [PMID:15113] [10.1021/jm00214a013]

Source

Source(1):

• Scientific Literature