1-[(5S,8S,15R,18R)-5,8-bis(4-aminobutyl)-18-(2-cyclohexylethyl)-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: ALA5196613

Chembl Id: CHEMBL5196613

PubChem CID: 168286328

Max Phase: Preclinical

Molecular Formula: C39H63F3N10O8

Molecular Weight: 742.97

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](CCC2CCCCC2)NC1=O.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C37H62N10O6.C2HF3O2/c38-18-6-4-13-28-34(50)43-24-53-20-17-31(47-37(40)41)36(52)46-30(16-15-25-9-2-1-3-10-25)33(49)42-23-27-12-8-11-26(21-27)22-32(48)44-29(35(51)45-28)14-5-7-19-39;3-2(4,5)1(6)7/h8,11-12,21,25,28-31H,1-7,9-10,13-20,22-24,38-39H2,(H,42,49)(H,43,50)(H,44,48)(H,45,51)(H,46,52)(H4,40,41,47);(H,6,7)/t28-,29-,30+,31+;/m0./s1

Standard InChI Key:  XAUHBKRWCRVNSI-PMAQQVHKSA-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: 742.97

Molecular Weight (Monoisotopic): 742.4854

AlogP: 0.26

#Rotatable Bonds: 12

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: 11.74

CX Basic pKa: 10.99

CX LogP: -0.91

CX LogD: -8.02

Aromatic Rings: 1

Heavy Atoms: 53

QED Weighted: 0.08

Np Likeness Score: 0.83

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