1-[(5S,8S,15R,18R)-5,8-bis(4-aminobutyl)-18-isobutyl-3,6,9,16,19-pentaoxo-12-oxa-4,7,10,17,20-pentazabicyclo[20.3.1]hexacosa-1(26),22,24-trien-15-yl]guanidine1-[(5S,8S,15R,18R)-5,8-bis(4-aminobutyl)-18-isobutyl-3,6,9,16,19-pentaoxo-12-oxa-4,7,10,17,20-pentazabicyclo[20.3.1]hexacosa-1(26),22,24-trien-15-yl]guanidine trifluoroacetate

ID: ALA5199482

Chembl Id: CHEMBL5199482

PubChem CID: 168292155

Max Phase: Preclinical

Molecular Formula: C35H57F3N10O8

Molecular Weight: 688.88

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H]1NC(=O)[C@H](NC(=N)N)CCOCNC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)Cc2cccc(c2)CNC1=O.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C33H56N10O6.C2HF3O2/c1-21(2)16-27-30(46)38-19-23-9-7-8-22(17-23)18-28(44)40-25(11-4-6-14-35)31(47)41-24(10-3-5-13-34)29(45)39-20-49-15-12-26(32(48)42-27)43-33(36)37;3-2(4,5)1(6)7/h7-9,17,21,24-27H,3-6,10-16,18-20,34-35H2,1-2H3,(H,38,46)(H,39,45)(H,40,44)(H,41,47)(H,42,48)(H4,36,37,43);(H,6,7)/t24-,25-,26+,27+;/m0./s1

Standard InChI Key:  YQFXAHYFHBKNQZ-GHXHZZECSA-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: 688.88

Molecular Weight (Monoisotopic): 688.4384

AlogP: -1.05

#Rotatable Bonds: 11

Polar Surface Area: 268.67

Molecular Species: BASE

HBA: 9

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.72

CX Basic pKa: 11.04

CX LogP: -2.26

CX LogD: -9.34

Aromatic Rings: 1

Heavy Atoms: 49

QED Weighted: 0.08

Np Likeness Score: 0.99

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