1-[(5S,8S,11R,21R)-5,8-bis(4-aminobutyl)-11-benzyl-4,7,10,13,17,20-hexaoxo-1-oxa-3,6,9,12,16,19-hexazacyclotricos-21-yl]guanidine trifluoroacetate

ID: ALA5196158

Chembl Id: CHEMBL5196158

PubChem CID: 168284762

Max Phase: Preclinical

Molecular Formula: C34H54F3N11O9

Molecular Weight: 703.85

Names and Identifiers

Canonical SMILES:  N=C(N)N[C@@H]1CCOCNC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2ccccc2)NC(=O)CCNC(=O)CNC1=O.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C32H53N11O7.C2HF3O2/c33-14-6-4-10-22-29(47)39-20-50-17-13-24(43-32(35)36)28(46)38-19-27(45)37-16-12-26(44)40-25(18-21-8-2-1-3-9-21)31(49)42-23(30(48)41-22)11-5-7-15-34;3-2(4,5)1(6)7/h1-3,8-9,22-25H,4-7,10-20,33-34H2,(H,37,45)(H,38,46)(H,39,47)(H,40,44)(H,41,48)(H,42,49)(H4,35,36,43);(H,6,7)/t22-,23-,24+,25+;/m0./s1

Standard InChI Key:  LTMBHIMCMDDIJT-UDRIRSMNSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 703.85

Molecular Weight (Monoisotopic): 703.4129

AlogP: -3.09

#Rotatable Bonds: 11

Polar Surface Area: 297.77

Molecular Species: BASE

HBA: 10

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 14

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.66

CX Basic pKa: 11.05

CX LogP: -4.62

CX LogD: -11.69

Aromatic Rings: 1

Heavy Atoms: 50

QED Weighted: 0.06

Np Likeness Score: 0.67

References

1. Huber S, Braun NJ, Schmacke LC, Quek JP, Murra R, Bender D, Hildt E, Luo D, Heine A, Steinmetzer T..  (2022)  Structure-Based Optimization and Characterization of Macrocyclic Zika Virus NS2B-NS3 Protease Inhibitors.,  65  (9.0): [PMID:35475620] [10.1021/acs.jmedchem.1c01860]

Source

Source(1):

• Scientific Literature