ID: ALA3344364

Max Phase: Preclinical

Molecular Formula: C34H50ClN7O6

Molecular Weight: 688.27

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)OCc1ccccc1)[C@@H](O)CC(=O)N(C)CCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C34H50ClN7O6/c1-22(2)19-28(29(43)20-30(44)42(4)18-16-24-12-14-26(35)15-13-24)40-31(45)23(3)39-32(46)27(11-8-17-38-33(36)37)41-34(47)48-21-25-9-6-5-7-10-25/h5-7,9-10,12-15,22-23,27-29,43H,8,11,16-21H2,1-4H3,(H,39,46)(H,40,45)(H,41,47)(H4,36,37,38)/t23-,27-,28-,29-/m0/s1

Standard InChI Key:  DNZNBEZRKTXBCA-HPEBZSCQSA-N

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

Properties

Molecular Weight: 688.27

Molecular Weight (Monoisotopic): 687.3511

AlogP: 2.69

#Rotatable Bonds: 19

Polar Surface Area: 198.97

Molecular Species: BASE

HBA: 7

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.48

CX Basic pKa: 11.85

CX LogP: 2.24

CX LogD: 0.15

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.07

Np Likeness Score: -0.17

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. Gazdik M, O'Neill MT, Lopaticki S, Lowes KN, Smith BJ, Cowman AF, Boddey JA, Sleebs BE.  (2015)  The effect of N-methylation on transition state mimetic inhibitors of the Plasmodium protease, plasmepsin V,  6  (3): [10.1039/C4MD00409D]

Source

Source(1):

• Scientific Literature