N-({[(S)-2-((R)-3-Hydroxy-pyrrolidin-1-yl)-1-phenyl-ethyl]-methyl-carbamoyl}-methyl)-2-methoxy-benzamide

ID: ALA179627

PubChem CID: 44389964

Max Phase: Preclinical

Molecular Formula: C23H29N3O4

Molecular Weight: 411.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1C(=O)NCC(=O)N(C)[C@H](CN1CC[C@@H](O)C1)c1ccccc1

Standard InChI:  InChI=1S/C23H29N3O4/c1-25(22(28)14-24-23(29)19-10-6-7-11-21(19)30-2)20(17-8-4-3-5-9-17)16-26-13-12-18(27)15-26/h3-11,18,20,27H,12-16H2,1-2H3,(H,24,29)/t18-,20-/m1/s1

Standard InChI Key:  PXPJOAVITOEIEW-UYAOXDASSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  1  0  0  0  0  0999 V2000
   -2.7833   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -0.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375   -0.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -0.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -1.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750    0.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -1.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000    1.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042    2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  1  0
  4  2  1  0
  5  8  1  0
  6  9  1  0
  7  3  1  0
  8  4  1  0
  9  7  1  0
 10  1  1  0
 11  3  2  0
 12  6  2  0
  4 13  1  1
 14  5  1  0
 15  5  1  0
 16 15  1  0
 17 14  1  0
 18  1  2  0
 19 10  1  0
 20  2  1  0
 17 21  1  6
 22 10  2  0
 23 13  1  0
 24 13  2  0
 25 19  1  0
 26 18  1  0
 27 24  1  0
 28 26  2  0
 29 23  2  0
 30 27  2  0
 28 22  1  0
 30 29  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA179627

   N-({[(S)-2-((R)-3-Hydroxy-pyrrolidin-1-yl)-1-phenyl-ethyl]-methyl-carbamoyl}-methyl)-2-methoxy-benzamide

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: 411.50

Molecular Weight (Monoisotopic): 411.2158

AlogP: 1.69

#Rotatable Bonds: 8

Polar Surface Area: 82.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.17

CX LogP: 1.07

CX LogD: 0.23

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: -1.01

References

1. Kumar V, Guo D, Daubert JD, Cassel JA, DeHaven RN, Mansson E, DeHaven-Hudkins DL, Maycock AL..  (2005)  Amino acid conjugates as kappa opioid receptor agonists.,  15  (5): [PMID:15713370] [10.1016/j.bmcl.2005.01.038]

Source

Source(1):

• Scientific Literature