ID: ALA486232

Max Phase: Preclinical

Molecular Formula: C28H37N3O5S

Molecular Weight: 527.69

Molecule Type: Small molecule

Representations

Synonyms (1): GNF-Pf-5434
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)C[C@H](NC(=O)N1CCOCC1)C(=O)N[C@H](/C=C/S(=O)(=O)c1ccccc1)CCc1ccccc1

Standard InChI:  InChI=1S/C28H37N3O5S/c1-22(2)21-26(30-28(33)31-16-18-36-19-17-31)27(32)29-24(14-13-23-9-5-3-6-10-23)15-20-37(34,35)25-11-7-4-8-12-25/h3-12,15,20,22,24,26H,13-14,16-19,21H2,1-2H3,(H,29,32)(H,30,33)/b20-15+/t24-,26-/m0/s1

Standard InChI Key:  YUMYYTORLYHUFW-MSKIIMLESA-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: 527.69

Molecular Weight (Monoisotopic): 527.2454

AlogP: 3.55

#Rotatable Bonds: 11

Polar Surface Area: 104.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.94

CX Basic pKa:

CX LogP: 3.49

CX LogD: 3.49

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.47

Np Likeness Score: -0.61

References

1. Verissimo E, Berry N, Gibbons P, Cristiano ML, Rosenthal PJ, Gut J, Ward SA, O'Neill PM..  (2008)  Design and synthesis of novel 2-pyridone peptidomimetic falcipain 2/3 inhibitors.,  18  (14): [PMID:18554905] [10.1016/j.bmcl.2008.05.068]

2. Li J, Petrassi HM, Tumanut C, Masick BT, Trussell C, Harris JL..  (2009)  Substrate optimization for monitoring cathepsin C activity in live cells.,  17  (3): [PMID:18313933] [10.1016/j.bmc.2008.02.002]

3. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

4. Capela R, Oliveira R, Gonçalves LM, Domingos A, Gut J, Rosenthal PJ, Lopes F, Moreira R..  (2009)  Artemisinin-dipeptidyl vinyl sulfone hybrid molecules: design, synthesis and preliminary SAR for antiplasmodial activity and falcipain-2 inhibition.,  19  (12): [PMID:19435664] [10.1016/j.bmcl.2009.04.100]

5. Ettari R, Tamborini L, Angelo IC, Micale N, Pinto A, De Micheli C, Conti P..  (2013)  Inhibition of rhodesain as a novel therapeutic modality for human African trypanosomiasis.,  56  (14): [PMID:23611656] [10.1021/jm301424d]

6. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(3):

• Scientific Literature
• Novartis Malaria Screening
• AstraZeneca Deposited Data