(3S,4S)-4-((S)-2-((S)-5-guanidino-2-(phenylmethylsulfonamido)pentanamido)-3-methylbutanamido)-3-hydroxy-6-methyl-N-phenethylheptanamide 2,2,2-trifluoroacetate

ID: ALA3344272

PubChem CID: 75593288

Max Phase: Preclinical

Molecular Formula: C36H54F3N7O8S

Molecular Weight: 687.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NS(=O)(=O)Cc1ccccc1)C(C)C)[C@@H](O)CC(=O)NCCc1ccccc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C34H53N7O6S.C2HF3O2/c1-23(2)20-28(29(42)21-30(43)37-19-17-25-12-7-5-8-13-25)39-33(45)31(24(3)4)40-32(44)27(16-11-18-38-34(35)36)41-48(46,47)22-26-14-9-6-10-15-26;3-2(4,5)1(6)7/h5-10,12-15,23-24,27-29,31,41-42H,11,16-22H2,1-4H3,(H,37,43)(H,39,45)(H,40,44)(H4,35,36,38);(H,6,7)/t27-,28-,29-,31-;/m0./s1

Standard InChI Key:  IMOBLHMHUQICCG-XCUOUWGKSA-N

Molfile:  

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M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 687.91

Molecular Weight (Monoisotopic): 687.3778

AlogP: 1.52

#Rotatable Bonds: 21

Polar Surface Area: 215.60

Molecular Species: BASE

HBA: 7

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.38

CX Basic pKa: 11.71

CX LogP: 1.32

CX LogD: -0.37

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.05

Np Likeness Score: -0.04

References

1. Sleebs BE, Gazdik M, O'Neill MT, Rajasekaran P, Lopaticki S, Lackovic K, Lowes K, Smith BJ, Cowman AF, Boddey JA..  (2014)  Transition state mimetics of the Plasmodium export element are potent inhibitors of Plasmepsin V from P. falciparum and P. vivax.,  57  (18): [PMID:25167370] [10.1021/jm500797g]

2. Nguyen W, Hodder AN, de Lezongard RB, Czabotar PE, Jarman KE, O'Neill MT, Thompson JK, Jousset Sabroux H, Cowman AF, Boddey JA, Sleebs BE..  (2018)  Enhanced antimalarial activity of plasmepsin V inhibitors by modification of the P2 position of PEXEL peptidomimetics.,  154  [PMID:29800827] [10.1016/j.ejmech.2018.05.022]

Source

Source(1):

• Scientific Literature