N-(1-Hydroxy-3-{4-[4-(2-oxo-2H-quinolin-1-yl)-piperidine-1-carbonyl]-phenoxy}-propyl)-acetamide

ID: ALA46419

PubChem CID: 15285181

Max Phase: Preclinical

Molecular Formula: C26H29N3O5

Molecular Weight: 463.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NC(O)CCOc1ccc(C(=O)N2CCC(n3c(=O)ccc4ccccc43)CC2)cc1

Standard InChI:  InChI=1S/C26H29N3O5/c1-18(30)27-24(31)14-17-34-22-9-6-20(7-10-22)26(33)28-15-12-21(13-16-28)29-23-5-3-2-4-19(23)8-11-25(29)32/h2-11,21,24,31H,12-17H2,1H3,(H,27,30)

Standard InChI Key:  XLAAEQOWWZDYNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    0.6792    1.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -1.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375    1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    2.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792    2.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792    0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -6.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -7.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    2.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3875   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1167    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -7.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -6.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -3.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -7.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    2.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625    1.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625    2.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4 15  1  0
  5  1  1  0
  6  2  1  0
  7 11  1  0
  8  1  1  0
  9 18  1  0
 10  9  1  0
 11  5  1  0
 12  3  1  0
 13  8  1  0
 14  8  1  0
 15 14  1  0
 16 13  1  0
 17  3  2  0
 18 20  1  0
 19  2  2  0
 20 25  1  0
 21 10  2  0
 22 12  2  0
 23 12  1  0
 24 27  1  0
 25 29  1  0
 26 22  1  0
 27 23  2  0
 28 18  1  0
 29 24  1  0
 30  5  2  0
 31 10  1  0
 32 11  2  0
 33 30  1  0
 34 33  2  0
  4 16  1  0
  7  6  2  0
 34 32  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA46419

   N-[1-hydroxy-3-[4-[4-(2-oxoquinolin-1-yl)piperidine-1-carbonyl]phenoxy]propyl]acetamide

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: 463.53

Molecular Weight (Monoisotopic): 463.2107

AlogP: 2.70

#Rotatable Bonds: 7

Polar Surface Area: 100.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.59

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: 1.34

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.52

Np Likeness Score: -0.91

References

1. Otsubo K, Morita S, Uchida M.  (1993)  Synthesis of N-Acetylhemiaminal metabolites of opc-21268, vasopressin V1 receptor antagonist,  3  (8): [10.1016/S0960-894X(00)80032-3]

Source

Source(1):

• Scientific Literature