benzyl (4-aminophenyl)(diphenoxyphosphoryl)methylcarbamate

ID: ALA3770879

Chembl Id: CHEMBL3770879

PubChem CID: 72163524

Max Phase: Preclinical

Molecular Formula: C27H25N2O5P

Molecular Weight: 488.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(C(NC(=O)OCc2ccccc2)P(=O)(Oc2ccccc2)Oc2ccccc2)cc1

Standard InChI:  InChI=1S/C27H25N2O5P/c28-23-18-16-22(17-19-23)26(29-27(30)32-20-21-10-4-1-5-11-21)35(31,33-24-12-6-2-7-13-24)34-25-14-8-3-9-15-25/h1-19,26H,20,28H2,(H,29,30)

Standard InChI Key:  ALYNXQPRNHJMPO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3770879

   benzyl N-[(4-aminophenyl)-diphenoxyphosphorylmethyl]carbamate

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: 488.48

Molecular Weight (Monoisotopic): 488.1501

AlogP: 6.54

#Rotatable Bonds: 9

Polar Surface Area: 99.88

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.96

CX Basic pKa: 4.04

CX LogP: 5.90

CX LogD: 5.90

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.20

Np Likeness Score: -0.26

References

1. van Soom J, Cuzzucoli Crucitti G, Gladysz R, van der Veken P, Di Santo R, Stuyver I, Buck V, Lambeir A, Magdolen V, Joossens J, Augustyns K.  (2015)  The first potent diphenyl phosphonate KLK4 inhibitors with unexpected binding kinetics,  6  (11): [10.1039/C5MD00288E]

2. Moreno-Cinos C, Sassetti E, Salado IG, Witt G, Benramdane S, Reinhardt L, Cruz CD, Joossens J, Van der Veken P, Brötz-Oesterhelt H, Tammela P, Winterhalter M, Gribbon P, Windshügel B, Augustyns K..  (2019)  α-Amino Diphenyl Phosphonates as Novel Inhibitors of Escherichia coli ClpP Protease.,  62  (2): [PMID:30571121] [10.1021/acs.jmedchem.8b01466]

Source

Source(1):

• Scientific Literature