N-((S)-1-((2S,3S)-3-hydroxy-5-oxo-5-((S)-1-oxo-3-phenyl-1-(prop-2-ynylamino)propan-2-ylamino)-1-phenylpentan-2-ylamino)-3-methyl-1-oxobutan-2-yl)picolinamide

ID: ALA1098671

Chembl Id: CHEMBL1098671

PubChem CID: 46236814

Max Phase: Preclinical

Molecular Formula: C34H39N5O5

Molecular Weight: 597.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCNC(=O)[C@H](Cc1ccccc1)NC(=O)C[C@H](O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)c1ccccn1)C(C)C

Standard InChI:  InChI=1S/C34H39N5O5/c1-4-18-36-32(42)28(21-25-15-9-6-10-16-25)37-30(41)22-29(40)27(20-24-13-7-5-8-14-24)38-34(44)31(23(2)3)39-33(43)26-17-11-12-19-35-26/h1,5-17,19,23,27-29,31,40H,18,20-22H2,2-3H3,(H,36,42)(H,37,41)(H,38,44)(H,39,43)/t27-,28-,29-,31-/m0/s1

Standard InChI Key:  RAZZBARIWRCYLK-KECWCRPSSA-N

Alternative Forms

1. Parent:

   

   ALA1098671

   N-((S)-1-((2S,3S)-3-hydroxy-5-oxo-5-((S)-1-oxo-3-phenyl-1-(prop-2-ynylamino)propan-2-ylamino)-1-phenylpentan-2-ylamino)-3-methyl-1-oxobutan-2-yl)picolinamide

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: 597.72

Molecular Weight (Monoisotopic): 597.2951

AlogP: 1.79

#Rotatable Bonds: 15

Polar Surface Area: 149.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.31

CX Basic pKa: 2.10

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.17

Np Likeness Score: -0.34

References

1. Gupta D, Yedidi RS, Varghese S, Kovari LC, Woster PM..  (2010)  Mechanism-based inhibitors of the aspartyl protease plasmepsin II as potential antimalarial agents.,  53  (10): [PMID:20438064] [10.1021/jm100233b]

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