ID: ALA1689148

Max Phase: Preclinical

Molecular Formula: C16H24N2O4

Molecular Weight: 308.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCC[C@H](NC(=O)[C@@H](O)[C@H](N)Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C16H24N2O4/c1-2-3-9-13(16(21)22)18-15(20)14(19)12(17)10-11-7-5-4-6-8-11/h4-8,12-14,19H,2-3,9-10,17H2,1H3,(H,18,20)(H,21,22)/t12-,13+,14+/m1/s1

Standard InChI Key:  SVYBIBUBSIRAHX-RDBSUJKOSA-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: 308.38

Molecular Weight (Monoisotopic): 308.1736

AlogP: 0.68

#Rotatable Bonds: 9

Polar Surface Area: 112.65

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.73

CX Basic pKa: 8.35

CX LogP: -0.94

CX LogD: -0.98

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.54

Np Likeness Score: 0.45

References

1. Velmourougane G, Harbut MB, Dalal S, McGowan S, Oellig CA, Meinhardt N, Whisstock JC, Klemba M, Greenbaum DC..  (2011)  Synthesis of new (-)-bestatin-based inhibitor libraries reveals a novel binding mode in the S1 pocket of the essential malaria M1 metalloaminopeptidase.,  54  (6): [PMID:21366301] [10.1021/jm101227t]

2. Nishizawa R, Saino T, Takita T, Suda H, Aoyagi T..  (1977)  Synthesis and structure-activity relationships of bestatin analogues, inhibitors of aminopeptidase B.,  20  (4): [PMID:850237] [10.1021/jm00214a010]

Source

Source(1):

• Scientific Literature