S-(S)-5-guanidino-2-((S)-2-(4-methylpiperazine-1-carboxamido)-3-phenylpropanamido)pentyl 4-nitrobenzenesulfonothioate bis(2,2,2-trifluoroacetate)

ID: ALA4742162

PubChem CID: 162645362

Max Phase: Preclinical

Molecular Formula: C31H40F6N8O10S2

Molecular Weight: 634.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CCN(C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCCNC(=N)N)CSS(=O)(=O)c2ccc([N+](=O)[O-])cc2)CC1.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C27H38N8O6S2.2C2HF3O2/c1-33-14-16-34(17-15-33)27(37)32-24(18-20-6-3-2-4-7-20)25(36)31-21(8-5-13-30-26(28)29)19-42-43(40,41)23-11-9-22(10-12-23)35(38)39;2*3-2(4,5)1(6)7/h2-4,6-7,9-12,21,24H,5,8,13-19H2,1H3,(H,31,36)(H,32,37)(H4,28,29,30);2*(H,6,7)/t21-,24-;;/m0../s1

Standard InChI Key:  ZBZVXKTWUCIGHS-XQXCFHDDSA-N

Molfile:  

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M  CHG  2  44   1  46  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 634.79

Molecular Weight (Monoisotopic): 634.2356

AlogP: 1.33

#Rotatable Bonds: 14

Polar Surface Area: 203.86

Molecular Species: BASE

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 11.79

CX LogP: 1.35

CX LogD: -1.22

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.05

Np Likeness Score: -0.73

References

1. Ward DJ,Van de Langemheen H,Koehne E,Kreidenweiss A,Liskamp RMJ.  (2019)  Highly tunable thiosulfonates as a novel class of cysteine protease inhibitors with anti-parasitic activity against Schistosoma mansoni.,  27  (13.0): [PMID:31126821] [10.1016/j.bmc.2019.05.014]

Source

Source(1):

• Scientific Literature