(R)-2-(2,6-dimethoxyphenoxy)-ethylaminomethyl-1,4-benzodioxane

ID: ALA214986

Chembl Id: CHEMBL214986

PubChem CID: 49797185

Max Phase: Preclinical

Molecular Formula: C19H24ClNO5

Molecular Weight: 345.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(OC)c1OCCNC[C@@H]1COc2ccccc2O1.Cl

Standard InChI:  InChI=1S/C19H23NO5.ClH/c1-21-17-8-5-9-18(22-2)19(17)23-11-10-20-12-14-13-24-15-6-3-4-7-16(15)25-14;/h3-9,14,20H,10-13H2,1-2H3;1H/t14-;/m1./s1

Standard InChI Key:  KAHMEWANVDFFCQ-PFEQFJNWSA-N

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: 345.40

Molecular Weight (Monoisotopic): 345.1576

AlogP: 2.51

#Rotatable Bonds: 8

Polar Surface Area: 58.18

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.76

CX LogP: 2.51

CX LogD: 1.14

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -0.20

References

1. Pallavicini M, Budriesi R, Fumagalli L, Ioan P, Chiarini A, Bolchi C, Ugenti MP, Colleoni S, Gobbi M, Valoti E..  (2006)  WB4101-related compounds: new, subtype-selective alpha1-adrenoreceptor antagonists (or inverse agonists?).,  49  (24): [PMID:17125266] [10.1021/jm060358r]

2. Fumagalli L, Pallavicini M, Budriesi R, Gobbi M, Straniero V, Zagami M, Chiodini G, Bolchi C, Chiarini A, Micucci M, Valoti E..  (2012)  Affinity and activity profiling of unichiral 8-substituted 1,4-benzodioxane analogues of WB4101 reveals a potent and selective α1B-adrenoceptor antagonist.,  58  [PMID:23124215] [10.1016/j.ejmech.2012.09.049]

3. Nelson WL, Powell ML, Dyer DC..  (1979)  Absolute configuration of glycerol derivatives. 7. Enantiomers of 2-[[[2-(2,6-dimethoxyphenoxy)ethyl]amino]methyl]-1,4-benzodioxane (WB-4101), a potent competitive alpha-adrenergic antagonist.,  22  (9): [PMID:40029] [10.1021/jm00195a024]

Source

Source(1):

• Scientific Literature