1,1'-(3-Methylphenylene-1,2-dioxy)bis(3-isopropylamino-2-propanol)dihydrochloride

ID: ALA3272435

PubChem CID: 90677515

Max Phase: Preclinical

Molecular Formula: C19H35ClN2O4

Molecular Weight: 354.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(OCC(O)CNC(C)C)c1OCC(O)CNC(C)C.Cl

Standard InChI:  InChI=1S/C19H34N2O4.ClH/c1-13(2)20-9-16(22)11-24-18-8-6-7-15(5)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:  GIUXYKYFRLUCHD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 25  0  0  0  0  0  0  0  0999 V2000
   20.4012   -4.0149    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.5276   -2.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5264   -3.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2412   -3.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9576   -3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9548   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2394   -1.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6728   -3.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6677   -1.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3837   -2.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0966   -1.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8126   -2.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0935   -1.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3865   -3.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1017   -3.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1030   -4.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8157   -3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5255   -1.9203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5357   -3.5632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5470   -4.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2671   -4.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8383   -4.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2415   -2.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9544   -1.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2446   -3.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2410   -4.4151    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
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: -0.26

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