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

ID: ALA3272437

PubChem CID: 90677517

Max Phase: Preclinical

Molecular Formula: C19H35ClN2O4

Molecular Weight: 354.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(OCC(O)CNC(C)C)c(OCC(O)CNC(C)C)c1.Cl

Standard InChI:  InChI=1S/C19H34N2O4.ClH/c1-13(2)20-9-16(22)11-24-18-7-6-15(5)8-19(18)25-12-17(23)10-21-14(3)4;/h6-8,13-14,16-17,20-23H,9-12H2,1-5H3;1H

Standard InChI Key:  UBLVDYJQNQEECO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 25  0  0  0  0  0  0  0  0999 V2000
   22.0702  -11.0818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.0028   -9.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0017  -10.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7165  -10.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4330  -10.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4301   -9.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7147   -8.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1481  -10.5883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1430   -8.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8590   -9.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5720   -8.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2879   -9.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5688   -8.1008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8619  -10.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5770  -10.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5783  -11.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2911  -10.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0009   -8.9204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0112  -10.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0225  -11.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7425  -11.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3138  -11.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7170   -9.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4298   -8.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7200  -10.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2869  -10.5893    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
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: 354.49

Molecular Weight (Monoisotopic): 354.2519

AlogP: 1.47

#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: 1.73

CX LogD: -2.72

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.46

Np Likeness Score: -0.38

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