(S)-2-Amino-N-((R)-6-benzyl-1,2,3,4-tetrahydroquinolin-4-yl)-3-(4-hydroxy-2,6-dimethylphenyl)propanamide

ID: ALA2322568

Chembl Id: CHEMBL2322568

PubChem CID: 10320450

Max Phase: Preclinical

Molecular Formula: C27H31N3O2

Molecular Weight: 429.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N[C@@H]1CCNc2ccc(Cc3ccccc3)cc21

Standard InChI:  InChI=1S/C27H31N3O2/c1-17-12-21(31)13-18(2)22(17)16-24(28)27(32)30-26-10-11-29-25-9-8-20(15-23(25)26)14-19-6-4-3-5-7-19/h3-9,12-13,15,24,26,29,31H,10-11,14,16,28H2,1-2H3,(H,30,32)/t24-,26+/m0/s1

Standard InChI Key:  VTFUYBNMSGPAQU-AZGAKELHSA-N

Alternative Forms

1. Parent:

   

   ALA2322568

   (2S)-2-amino-N-[(4R)-6-benzyl-1,2,3,4-tetrahydroquinolin-4-yl]-3-(4-hydroxy-2,6-dimethylphenyl)propanamide

2. Alternative Forms:

   

   ALA2322568

   ---

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: 429.56

Molecular Weight (Monoisotopic): 429.2416

AlogP: 4.14

#Rotatable Bonds: 6

Polar Surface Area: 87.38

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.76

CX Basic pKa: 8.05

CX LogP: 4.34

CX LogD: 3.71

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: 0.38

References

1. Mosberg HI, Yeomans L, Harland AA, Bender AM, Sobczyk-Kojiro K, Anand JP, Clark MJ, Jutkiewicz EM, Traynor JR..  (2013)  Opioid peptidomimetics: leads for the design of bioavailable mixed efficacy μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist ligands.,  56  (5): [PMID:23419026] [10.1021/jm400050y]

2. Harland AA, Yeomans L, Griggs NW, Anand JP, Pogozheva ID, Jutkiewicz EM, Traynor JR, Mosberg HI..  (2015)  Further Optimization and Evaluation of Bioavailable, Mixed-Efficacy μ-Opioid Receptor (MOR) Agonists/δ-Opioid Receptor (DOR) Antagonists: Balancing MOR and DOR Affinities.,  58  (22): [PMID:26524472] [10.1021/acs.jmedchem.5b01270]

3. Harland AA, Bender AM, Griggs NW, Gao C, Anand JP, Pogozheva ID, Traynor JR, Jutkiewicz EM, Mosberg HI..  (2016)  Effects of N-Substitutions on the Tetrahydroquinoline (THQ) Core of Mixed-Efficacy μ-Opioid Receptor (MOR)/δ-Opioid Receptor (DOR) Ligands.,  59  (10): [PMID:27148755] [10.1021/acs.jmedchem.6b00308]

4. Henry SP, Fernandez TJ, Anand JP, Griggs NW, Traynor JR, Mosberg HI..  (2019)  Structural Simplification of a Tetrahydroquinoline-Core Peptidomimetic μ-Opioid Receptor (MOR) Agonist/δ-Opioid Receptor (DOR) Antagonist Produces Improved Metabolic Stability.,  62  (8): [PMID:30924650] [10.1021/acs.jmedchem.9b00219]

Source

Source(1):

• Scientific Literature