1-[(5S,8S,15R,18R)-5,8-bis(4-aminobutyl)-18-(cyclohexylmethyl)-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: ALA5209038

Chembl Id: CHEMBL5209038

PubChem CID: 168297747

Max Phase: Preclinical

Molecular Formula: C38H61F3N10O8

Molecular Weight: 728.94

Names and Identifiers

Canonical SMILES:  N=C(N)N[C@@H]1CCOCNC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)Cc2cccc(c2)CNC(=O)[C@@H](CC2CCCCC2)NC1=O.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C36H60N10O6.C2HF3O2/c37-16-6-4-13-27-32(48)42-23-52-18-15-29(46-36(39)40)35(51)45-30(20-24-9-2-1-3-10-24)33(49)41-22-26-12-8-11-25(19-26)21-31(47)43-28(34(50)44-27)14-5-7-17-38;3-2(4,5)1(6)7/h8,11-12,19,24,27-30H,1-7,9-10,13-18,20-23,37-38H2,(H,41,49)(H,42,48)(H,43,47)(H,44,50)(H,45,51)(H4,39,40,46);(H,6,7)/t27-,28-,29+,30+;/m0./s1

Standard InChI Key:  MDUSXMILNFIUNP-JDQRQYMYSA-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: 728.94

Molecular Weight (Monoisotopic): 728.4697

AlogP: -0.13

#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: 11.73

CX Basic pKa: 11.00

CX LogP: -1.36

CX LogD: -8.47

Aromatic Rings: 1

Heavy Atoms: 52

QED Weighted: 0.08

Np Likeness Score: 0.82

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