4-Acetamidophenyl 2-morpholinoacetate hydrochloride

ID: ALA1795483

PubChem CID: 56683373

Max Phase: Preclinical

Molecular Formula: C14H19ClN2O4

Molecular Weight: 278.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-Acetamidophenyl 2-Morpholinoacetate HCl | CHEMBL1795483|4-Acetamidophenyl 2-Morpholinoacetate HCl

Canonical SMILES:  CC(=O)Nc1ccc(OC(=O)CN2CCOCC2)cc1.Cl

Standard InChI:  InChI=1S/C14H18N2O4.ClH/c1-11(17)15-12-2-4-13(5-3-12)20-14(18)10-16-6-8-19-9-7-16;/h2-5H,6-10H2,1H3,(H,15,17);1H

Standard InChI Key:  FAYTUYGQHXCBKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    5.5125   -0.0313    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0243    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0243   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1677   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1677    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1191   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8336   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8336    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1191    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2625   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9770   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2625    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  2  0
  2  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6 11  1  0
  3  9  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 18 19  1  0
 18 20  2  0
 18 21  1  0
 15 21  1  0
  5 12  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: 278.31

Molecular Weight (Monoisotopic): 278.1267

AlogP: 0.88

#Rotatable Bonds: 4

Polar Surface Area: 67.87

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.21

CX LogP: 0.49

CX LogD: 0.49

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.65

Np Likeness Score: -1.71

References

1. Devarajan-Ketha H, Sloan KB..  (2011)  N,N'-Dialkylaminoalkylcarbonyl (DAAC) prodrugs and aminoalkylcarbonyl (AAC) prodrugs of 4-hydroxyacetanilide and naltrexone with improved skin permeation properties.,  21  (13): [PMID:21616664] [10.1016/j.bmcl.2011.04.118]

Source

Source(1):

• Scientific Literature