Diethyl(2R)-2-{[(2S)-2-({2-[(1H-Indol-2-ylcarbonyl)amino]-acetyl}amino)propanoyl]amino}pentanedioate

ID: ALA2163879

Chembl Id: CHEMBL2163879

PubChem CID: 60195105

Max Phase: Preclinical

Molecular Formula: C23H30N4O7

Molecular Weight: 474.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)CNC(=O)c1cc2ccccc2[nH]1)C(=O)OCC

Standard InChI:  InChI=1S/C23H30N4O7/c1-4-33-20(29)11-10-17(23(32)34-5-2)27-21(30)14(3)25-19(28)13-24-22(31)18-12-15-8-6-7-9-16(15)26-18/h6-9,12,14,17,26H,4-5,10-11,13H2,1-3H3,(H,24,31)(H,25,28)(H,27,30)/t14-,17+/m0/s1

Standard InChI Key:  XGWGCKIGQZSSPT-WMLDXEAASA-N

Alternative Forms

1. Parent:

   

   ALA2163879

   diethyl (2R)-2-[[(2S)-2-[[2-(1H-indole-2-carbonylamino)acetyl]amino]propanoyl]amino]pentanedioate

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: 474.51

Molecular Weight (Monoisotopic): 474.2114

AlogP: 0.79

#Rotatable Bonds: 12

Polar Surface Area: 155.69

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.91

CX Basic pKa:

CX LogP: 0.12

CX LogD: 0.12

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -0.68

References

1. Jakopin Ž, Gobec M, Mlinarič-Raščan I, Sollner Dolenc M..  (2012)  Immunomodulatory properties of novel nucleotide oligomerization domain 2 (nod2) agonistic desmuramyldipeptides.,  55  (14): [PMID:22716113] [10.1021/jm300503b]

2. 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]

Source

Source(1):

• Scientific Literature