benzyl (diphenoxyphosphoryl)(4-guanidinophenyl)methylcarbamate

ID: ALA1184949

Chembl Id: CHEMBL1184949

Max Phase: Preclinical

Molecular Formula: C28H27N4O5P

Molecular Weight: 530.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H27N4O5P/c29-27(30)31-23-18-16-22(17-19-23)26(32-28(33)35-20-21-10-4-1-5-11-21)38(34,36-24-12-6-2-7-13-24)37-25-14-8-3-9-15-25/h1-19,26H,20H2,(H,32,33)(H4,29,30,31)

Standard InChI Key:  RMJHMNZGTJDKCS-UHFFFAOYSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1184949

   benzyl N-[[4-(diaminomethylideneamino)phenyl]-diphenoxyphosphorylmethyl]carbamate;2,2,2-trifluoroacetic acid

2. Parent:

   

   ALA1184949

   ---

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: 530.52

Molecular Weight (Monoisotopic): 530.1719

AlogP: 6.27

#Rotatable Bonds: 10

Polar Surface Area: 135.76

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.91

CX Basic pKa: 9.95

CX LogP: 5.97

CX LogD: 3.75

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.11

Np Likeness Score: -0.34

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