ID: ALA327844

Max Phase: Preclinical

Molecular Formula: C19H24NO4P

Molecular Weight: 361.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  NC(CCc1ccccc1)P(=O)(O)CC(Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C19H24NO4P/c20-18(12-11-15-7-3-1-4-8-15)25(23,24)14-17(19(21)22)13-16-9-5-2-6-10-16/h1-10,17-18H,11-14,20H2,(H,21,22)(H,23,24)

Standard InChI Key:  QELOIXSGJMIHBZ-UHFFFAOYSA-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: 361.38

Molecular Weight (Monoisotopic): 361.1443

AlogP: 3.12

#Rotatable Bonds: 9

Polar Surface Area: 100.62

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: -0.06

CX Basic pKa: 9.92

CX LogP: 1.76

CX LogD: -0.92

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: 0.30

References

1. Grembecka J, Mucha A, Cierpicki T, Kafarski P..  (2003)  The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity.,  46  (13): [PMID:12801228] [10.1021/jm030795v]

2. Mucha A, Lämmerhofer M, Lindner W, Pawełczak M, Kafarski P..  (2008)  Individual stereoisomers of phosphinic dipeptide inhibitor of leucine aminopeptidase.,  18  (5): [PMID:18262419] [10.1016/j.bmcl.2008.01.107]

3. Deprez-Poulain R, Flipo M, Piveteau C, Leroux F, Dassonneville S, Florent I, Maes L, Cos P, Deprez B..  (2012)  Structure-activity relationships and blood distribution of antiplasmodial aminopeptidase-1 inhibitors.,  55  (24): [PMID:23176597] [10.1021/jm301506h]

4. Vassiliou S, Węglarz-Tomczak E, Berlicki Ł, Pawełczak M, Nocek B, Mulligan R, Joachimiak A, Mucha A..  (2014)  Structure-guided, single-point modifications in the phosphinic dipeptide structure yield highly potent and selective inhibitors of neutral aminopeptidases.,  57  (19): [PMID:25192493] [10.1021/jm501071f]

5. Węglarz-Tomczak E, Vassiliou S, Mucha A..  (2016)  Discovery of potent and selective inhibitors of human aminopeptidases ERAP1 and ERAP2 by screening libraries of phosphorus-containing amino acid and dipeptide analogues.,  26  (16): [PMID:27390066] [10.1016/j.bmcl.2016.06.062]

6. Talma M, Maślanka M, Mucha A..  (2019)  Recent developments in the synthesis and applications of phosphinic peptide analogs.,  29  (9): [PMID:30846252] [10.1016/j.bmcl.2019.02.034]

7. Mills B, Isaac RE, Foster R..  (2021)  Metalloaminopeptidases of the Protozoan Parasite Plasmodium falciparum as Targets for the Discovery of Novel Antimalarial Drugs.,  64  (4.0): [PMID:33534577] [10.1021/acs.jmedchem.0c01721]

Source

Source(1):

• Scientific Literature