N-{2-[2-Hydroxy-3-(2-nitro-phenoxy)-propylamino]-ethyl}-2,2-dimethyl-propionamide; compound with oxalic acid

ID: ALA3392269

PubChem CID: 13030883

Max Phase: Preclinical

Molecular Formula: C18H27N3O9

Molecular Weight: 339.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)NCCNCC(O)COc1ccccc1[N+](=O)[O-].O=C(O)C(=O)O

Standard InChI:  InChI=1S/C16H25N3O5.C2H2O4/c1-16(2,3)15(21)18-9-8-17-10-12(20)11-24-14-7-5-4-6-13(14)19(22)23;3-1(4)2(5)6/h4-7,12,17,20H,8-11H2,1-3H3,(H,18,21);(H,3,4)(H,5,6)

Standard InChI Key:  HGSMKLQQCBLMRP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 29  0  0  0  0  0  0  0  0999 V2000
    4.2134   -5.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0384   -5.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4509   -6.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4509   -4.7364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8009   -4.7364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8009   -6.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -2.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -3.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4375   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -1.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -0.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250    0.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -0.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -0.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    0.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  2  0
  1  6  1  0
  8  7  1  0
  9 16  1  0
 10  7  1  0
 11  8  2  0
 12  9  1  0
 13  7  2  0
 14 11  1  0
 15  9  2  0
 16 27  1  0
 17 14  1  0
 18 17  1  0
 19 25  1  0
 20  8  1  0
 21 18  1  0
 22 12  1  0
 23 12  1  0
 24 12  1  0
 25 18  1  0
 26 11  1  0
 27 28  1  0
 28 19  1  0
 29 20  2  0
 30 26  2  0
 30 29  1  0
M  CHG  2   7   1  10  -1
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: 339.39

Molecular Weight (Monoisotopic): 339.1794

AlogP: 1.09

#Rotatable Bonds: 9

Polar Surface Area: 113.73

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 1.58

CX LogD: 0.18

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.35

Np Likeness Score: -1.24

References

1. Lare MS, Smith LH..  (1982)  Beta-adrenergic blocking agents. 22. 1-Phenoxy-3-[[(substituted-amido) alkyl]amino]-2-propanols.,  25  (11): [PMID:6128420] [10.1021/jm00353a004]

Source

Source(1):

• Scientific Literature