4-(3-((2-(2-Methoxyphenoxy)ethyl)amino)propoxy)benzene-1,2-diol

ID: ALA4459541

PubChem CID: 155527582

Max Phase: Preclinical

Molecular Formula: C18H23NO5

Molecular Weight: 333.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1OCCNCCCOc1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C18H23NO5/c1-22-17-5-2-3-6-18(17)24-12-10-19-9-4-11-23-14-7-8-15(20)16(21)13-14/h2-3,5-8,13,19-21H,4,9-12H2,1H3

Standard InChI Key:  ISBAPZLLRFJIGB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   14.9174  -28.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6254  -29.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3351  -28.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3322  -27.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0384  -27.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7477  -27.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4538  -27.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1631  -27.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8692  -27.5777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5785  -27.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9185  -28.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6218  -27.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2108  -27.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2093  -29.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2846  -27.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9939  -27.9783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7000  -27.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4076  -27.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1133  -27.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1107  -26.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3964  -26.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6937  -26.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9828  -26.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9765  -25.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  2  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4 12  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 12  1  0
 11 13  1  0
  1 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4459541

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 333.38

Molecular Weight (Monoisotopic): 333.1576

AlogP: 2.54

#Rotatable Bonds: 10

Polar Surface Area: 80.18

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.67

CX Basic pKa: 9.06

CX LogP: 1.80

CX LogD: 0.52

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.46

Np Likeness Score: -0.09

References

1. Stanek M, Picard LP, Schmidt MF, Kaindl JM, Hübner H, Bouvier M, Weikert D, Gmeiner P..  (2019)  Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias.,  62  (10): [PMID:31042379] [10.1021/acs.jmedchem.9b00349]

Source

Source(1):

• Scientific Literature