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

ID: ALA3272436

PubChem CID: 90677516

Max Phase: Preclinical

Molecular Formula: C21H39ClN2O4

Molecular Weight: 382.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)NCC(O)COc1cccc(C(C)C)c1OCC(O)CNC(C)C.Cl

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

Standard InChI Key:  VWYVALTVNAZLLJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
   11.3101  -11.7565    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2610  -10.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2599  -10.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9747  -11.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6912  -10.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882  -10.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9729   -9.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062  -11.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012   -9.6311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1171  -10.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8301   -9.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5460  -10.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -8.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1201  -10.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8351  -11.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8364  -12.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5492  -10.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2590   -9.6203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2693  -11.2631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2806  -12.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0006  -12.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5719  -12.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9751  -10.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6879   -9.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9781  -10.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745  -12.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2599  -12.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888  -12.5277    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
  4 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: -0.12

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