2-[2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid phenylcarbamoylmethyl-amide

ID: ALA501451

Chembl Id: CHEMBL501451

PubChem CID: 11016572

Max Phase: Preclinical

Molecular Formula: C29H32N4O4

Molecular Weight: 500.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N1Cc2ccccc2C[C@H]1C(=O)NCC(=O)Nc1ccccc1

Standard InChI:  InChI=1S/C29H32N4O4/c1-18-12-23(34)13-19(2)24(18)15-25(30)29(37)33-17-21-9-7-6-8-20(21)14-26(33)28(36)31-16-27(35)32-22-10-4-3-5-11-22/h3-13,25-26,34H,14-17,30H2,1-2H3,(H,31,36)(H,32,35)/t25-,26-/m0/s1

Standard InChI Key:  JQERUKPESNWSQA-UIOOFZCWSA-N

Alternative Forms

1. Parent:

   

   ALA501451

   H-Dmt-Tic-Gly-NH-Ph

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: 500.60

Molecular Weight (Monoisotopic): 500.2424

AlogP: 2.59

#Rotatable Bonds: 7

Polar Surface Area: 124.76

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.75

CX Basic pKa: 7.75

CX LogP: 3.22

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.40

Np Likeness Score: -0.63

References

1. Balboni G, Guerrini R, Salvadori S, Bianchi C, Rizzi D, Bryant SD, Lazarus LH..  (2002)  Evaluation of the Dmt-Tic pharmacophore: conversion of a potent delta-opioid receptor antagonist into a potent delta agonist and ligands with mixed properties.,  45  (3): [PMID:11806723] [10.1021/jm010449i]

2. Ballet S, Salvadori S, Trapella C, Bryant SD, Jinsmaa Y, Lazarus LH, Negri L, Giannini E, Lattanzi R, Tourwé D, Balboni G..  (2006)  New 2',6'-dimethyl-L-tyrosine (Dmt) opioid peptidomimetics based on the Aba-Gly scaffold. Development of unique mu-opioid receptor ligands.,  49  (13): [PMID:16789756] [10.1021/jm0603264]

3. Balboni G, Fiorini S, Baldisserotto A, Trapella C, Sasaki Y, Ambo A, Marczak ED, Lazarus LH, Salvadori S..  (2008)  Further studies on lead compounds containing the opioid pharmacophore Dmt-Tic.,  51  (16): [PMID:18680274] [10.1021/jm800587e]

Source

Source(1):

• Scientific Literature