(2S)-3-(2-chlorophenyl)-2-(2-phenylacetamido)-N-(4-(((9R)-7,10,13,21-tetraoxo-8,11,14,20-tetraazaspiro[4.17]docosan-9-yl)methyl)phenyl)propanamide

ID: ALA3785600

Chembl Id: CHEMBL3785600

Cas Number: 1449208-36-9

PubChem CID: 117810400

Max Phase: Preclinical

Molecular Formula: C42H51ClN6O6

Molecular Weight: 771.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CNC(=O)[C@@H](Cc2ccc(NC(=O)[C@H](Cc3ccccc3Cl)NC(=O)Cc3ccccc3)cc2)NC(=O)CC2(CCCC2)CC(=O)NCCCCCN1

Standard InChI:  InChI=1S/C42H51ClN6O6/c43-33-14-6-5-13-31(33)25-35(48-36(50)24-29-11-3-1-4-12-29)41(55)47-32-17-15-30(16-18-32)23-34-40(54)46-28-39(53)45-22-10-2-9-21-44-37(51)26-42(19-7-8-20-42)27-38(52)49-34/h1,3-6,11-18,34-35H,2,7-10,19-28H2,(H,44,51)(H,45,53)(H,46,54)(H,47,55)(H,48,50)(H,49,52)/t34-,35+/m1/s1

Standard InChI Key:  HSTNEKZTSOZTDI-GPOMZPHUSA-N

Alternative Forms

1. Parent:

   

   ALA3785600

   (2S)-3-(2-chlorophenyl)-2-(2-phenylacetamido)-N-(4-(((9R)-7,10,13,21-tetraoxo-8,11,14,20-tetraazaspiro[4.17]docosan-9-yl)methyl)phenyl)propanamide

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: 771.36

Molecular Weight (Monoisotopic): 770.3559

AlogP: 4.15

#Rotatable Bonds: 9

Polar Surface Area: 174.60

Molecular Species: NEUTRAL

HBA: 6

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.07

CX Basic pKa: ┄

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 55

QED Weighted: 0.19

Np Likeness Score: -0.10

References

1. Espada A, Broughton H, Jones S, Chalmers MJ, Dodge JA..  (2016)  A Binding Site on IL-17A for Inhibitory Macrocycles Revealed by Hydrogen/Deuterium Exchange Mass Spectrometry.,  59  (5): [PMID:26854023] [10.1021/acs.jmedchem.5b01693]

2. Koštrun S, Fajdetić A, Pešić D, Brajša K, Bencetić Mihaljević V, Jelić D, Petrinić Grba A, Elenkov I, Rupčić R, Kapić S, Ozimec Landek I, Butković K, Grgičević A, Žiher D, Čikoš A, Padovan J, Saxty G, Dack K, Bladh H, Skak-Nielsen T, Feldbaek Nielsen S, Lambert M, Stahlhut M..  (2021)  Macrolide Inspired Macrocycles as Modulators of the IL-17A/IL-17RA Interaction.,  64  (12.0): [PMID:34100601] [10.1021/acs.jmedchem.1c00327]

3. Andrews MD, Dack KN, de Groot MJ, Lambert M, Sennbro CJ, Larsen M, Stahlhut M..  (2022)  Discovery of an Oral, Rule of 5 Compliant, Interleukin 17A Protein-Protein Interaction Modulator for the Potential Treatment of Psoriasis and Other Inflammatory Diseases.,  65  (13.0): [PMID:35767390] [10.1021/acs.jmedchem.2c00422]

Source

Source(1):

• Scientific Literature