phenacetyl KKR-acid

ID: ALA492694

PubChem CID: 44569041

Max Phase: Preclinical

Molecular Formula: C26H44N8O5

Molecular Weight: 548.69

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Phenacetyl Kkr-Acid | phenacetyl KKR-acid|CHEMBL492694

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

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA492694

   phenacetyl KKR-acid

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: 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