ID: ALA176888

Max Phase: Preclinical

Molecular Formula: C46H48N2O10

Molecular Weight: 788.89

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(=O)c1ccc(/C=C/CO[C@@H](C(=O)N[C@H]2c3ccccc3C[C@H]2O)[C@H](O)[C@@H](O)[C@@H](OC/C=C/c2ccc(C(C)=O)cc2)C(=O)N[C@H]2c3ccccc3C[C@H]2O)cc1

Standard InChI:  InChI=1S/C46H48N2O10/c1-27(49)31-19-15-29(16-20-31)9-7-23-57-43(45(55)47-39-35-13-5-3-11-33(35)25-37(39)51)41(53)42(54)44(58-24-8-10-30-17-21-32(22-18-30)28(2)50)46(56)48-40-36-14-6-4-12-34(36)26-38(40)52/h3-22,37-44,51-54H,23-26H2,1-2H3,(H,47,55)(H,48,56)/b9-7+,10-8+/t37-,38-,39+,40+,41-,42-,43-,44-/m1/s1

Standard InChI Key:  WZXYHEYYJRGWNR-VVKCFMERSA-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: 788.89

Molecular Weight (Monoisotopic): 788.3309

AlogP: 3.86

#Rotatable Bonds: 17

Polar Surface Area: 191.72

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.80

CX Basic pKa:

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 4

Heavy Atoms: 58

QED Weighted: 0.09

Np Likeness Score: 0.29

References

1. Ersmark K, Feierberg I, Bjelic S, Hamelink E, Hackett F, Blackman MJ, Hultén J, Samuelsson B, Aqvist J, Hallberg A..  (2004)  Potent inhibitors of the Plasmodium falciparum enzymes plasmepsin I and II devoid of cathepsin D inhibitory activity.,  47  (1): [PMID:14695825] [10.1021/jm030933g]

2. Cheuka PM, Dziwornu G, Okombo J, Chibale K..  (2020)  Plasmepsin Inhibitors in Antimalarial Drug Discovery: Medicinal Chemistry and Target Validation (2000 to Present).,  63  (9): [PMID:31913032] [10.1021/acs.jmedchem.9b01622]

Source

Source(1):

• Scientific Literature