ID: ALA492694

Max Phase: Preclinical

Molecular Formula: C26H44N8O5

Molecular Weight: 548.69

Molecule Type: Small molecule

Representations

Synonyms (1): Phenacetyl Kkr-Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C26H44N8O5/c27-14-6-4-11-19(32-22(35)17-18-9-2-1-3-10-18)23(36)33-20(12-5-7-15-28)24(37)34-21(25(38)39)13-8-16-31-26(29)30/h1-3,9-10,19-21H,4-8,11-17,27-28H2,(H,32,35)(H,33,36)(H,34,37)(H,38,39)(H4,29,30,31)/t19-,20-,21-/m0/s1

Standard InChI Key:  XHVGUCXLWRVFJQ-ACRUOGEOSA-N

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

Properties

Molecular Weight: 548.69

Molecular Weight (Monoisotopic): 548.3435

AlogP: -0.71

#Rotatable Bonds: 20

Polar Surface Area: 238.54

Molecular Species: ZWITTERION

HBA: 7

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.74

CX Basic pKa: 11.90

CX LogP: -3.00

CX LogD: -8.02

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.06

Np Likeness Score: 0.10

References

1. Stoermer MJ, Chappell KJ, Liebscher S, Jensen CM, Gan CH, Gupta PK, Xu WJ, Young PR, Fairlie DP..  (2008)  Potent cationic inhibitors of West Nile virus NS2B/NS3 protease with serum stability, cell permeability and antiviral activity.,  51  (18): [PMID:18729351] [10.1021/jm800503y]

2. Colarusso S, Ferrigno F, Ponzi S, Pavone F, Conte I, Abate L, Beghetto E, Missineo A, Amaudrut J, Bresciani A, Paonessa G, Tomei L, Montalbetti C, Bianchi E, Toniatti C, Ontoria JM..  (2022)  SAR evolution towards potent C-terminal carboxamide peptide inhibitors of Zika virus NS2B-NS3 protease.,  57  [PMID:35123179] [10.1016/j.bmc.2022.116631]

Source

Source(1):

• Scientific Literature