3,3'-(naphthalene-2,3-diylbis(oxy))bis(1-(isopropylamino)propan-2-ol)dihydrochloride

ID: ALA3272440

PubChem CID: 90677519

Max Phase: Preclinical

Molecular Formula: C22H35ClN2O4

Molecular Weight: 390.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)NCC(O)COc1cc2ccccc2cc1OCC(O)CNC(C)C.Cl

Standard InChI:  InChI=1S/C22H34N2O4.ClH/c1-15(2)23-11-19(25)13-27-21-9-17-7-5-6-8-18(17)10-22(21)28-14-20(26)12-24-16(3)4;/h5-10,15-16,19-20,23-26H,11-14H2,1-4H3;1H

Standard InChI Key:  KSMZYIAFEIFPGK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   24.5916  -17.0833    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.6541  -17.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3705  -16.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3676  -15.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6522  -15.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0856  -17.0134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0806  -15.3563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7966  -15.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5095  -15.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2255  -15.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5064  -14.5259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7995  -16.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5146  -17.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5159  -17.8362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2286  -16.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9384  -15.3455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9487  -16.9883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9600  -17.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6801  -18.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2513  -18.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6544  -15.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3674  -15.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6576  -16.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9392  -16.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9415  -15.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2289  -15.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5134  -15.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5151  -16.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2283  -17.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 24  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 25  1  0
  3  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  1  0
 10 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 21 23  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 24  2  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: 390.52

Molecular Weight (Monoisotopic): 390.2519

AlogP: 2.32

#Rotatable Bonds: 12

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: 2.20

CX LogD: -2.25

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -0.18

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