Diethyl (6-phenyl-1H-indole-2-carbonyl)glycyl-L-alanyl-D-glutamate

ID: ALA3798250

Chembl Id: CHEMBL3798250

PubChem CID: 127047056

Max Phase: Preclinical

Molecular Formula: C29H34N4O7

Molecular Weight: 550.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)CNC(=O)c1cc2ccc(-c3ccccc3)cc2[nH]1)C(=O)OCC

Standard InChI:  InChI=1S/C29H34N4O7/c1-4-39-26(35)14-13-22(29(38)40-5-2)33-27(36)18(3)31-25(34)17-30-28(37)24-16-21-12-11-20(15-23(21)32-24)19-9-7-6-8-10-19/h6-12,15-16,18,22,32H,4-5,13-14,17H2,1-3H3,(H,30,37)(H,31,34)(H,33,36)/t18-,22+/m0/s1

Standard InChI Key:  COSLQJTWFNRSPT-PGRDOPGGSA-N

Alternative Forms

1. Parent:

   

   ALA3798250

   ---

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: 550.61

Molecular Weight (Monoisotopic): 550.2427

AlogP: 2.46

#Rotatable Bonds: 13

Polar Surface Area: 155.69

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.93

CX Basic pKa:

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.24

Np Likeness Score: -0.64

References

1. Gobec M, Mlinarič-Raščan I, Dolenc MS, Jakopin Ž..  (2016)  Structural requirements of acylated Gly-l-Ala-d-Glu analogs for activation of the innate immune receptor NOD2.,  116  [PMID:27039337] [10.1016/j.ejmech.2016.03.030]

2. Gobec M, Tomašič T, Štimac A, Frkanec R, Trontelj J, Anderluh M, Mlinarič-Raščan I, Jakopin Ž..  (2018)  Discovery of Nanomolar Desmuramylpeptide Agonists of the Innate Immune Receptor Nucleotide-Binding Oligomerization Domain-Containing Protein 2 (NOD2) Possessing Immunostimulatory Properties.,  61  (7): [PMID:29543461] [10.1021/acs.jmedchem.7b01052]

Source

Source(1):

• Scientific Literature