[Benzyloxycarbonylamino-(4-carbamimidoyl-phenyl)-methyl]-phosphonic acid diphenyl ester

ID: ALA238707

Chembl Id: CHEMBL238707

PubChem CID: 9827867

Max Phase: Preclinical

Molecular Formula: C28H26N3O5P

Molecular Weight: 515.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(C(NC(=O)OCc2ccccc2)P(=O)(Oc2ccccc2)Oc2ccccc2)cc1

Standard InChI:  InChI=1S/C28H26N3O5P/c29-26(30)22-16-18-23(19-17-22)27(31-28(32)34-20-21-10-4-1-5-11-21)37(33,35-24-12-6-2-7-13-24)36-25-14-8-3-9-15-25/h1-19,27H,20H2,(H3,29,30)(H,31,32)

Standard InChI Key:  WYCVSPRVSFUVMA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA238707

   Diphenyl N-(benzyloxycarbonyl)amino(4-amidinophenyl)methanephosphonate

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: 515.51

Molecular Weight (Monoisotopic): 515.1610

AlogP: 6.25

#Rotatable Bonds: 10

Polar Surface Area: 123.73

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.86

CX Basic pKa: 11.45

CX LogP: 5.53

CX LogD: 3.21

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.13

Np Likeness Score: -0.21

References

1. Jackson DS, Fraser SA, Ni LM, Kam CM, Winkler U, Johnson DA, Froelich CJ, Hudig D, Powers JC..  (1998)  Synthesis and evaluation of diphenyl phosphonate esters as inhibitors of the trypsin-like granzymes A and K and mast cell tryptase.,  41  (13): [PMID:9632362] [10.1021/jm970543s]

2. Oleksyszyn J, Boduszek B, Kam CM, Powers JC..  (1994)  Novel amidine-containing peptidyl phosphonates as irreversible inhibitors for blood coagulation and related serine proteases.,  37  (2): [PMID:8295209] [10.1021/jm00028a004]

3. Joossens J, Ali OM, El-Sayed I, Surpateanu G, Van der Veken P, Lambeir AM, Setyono-Han B, Foekens JA, Schneider A, Schmalix W, Haemers A, Augustyns K..  (2007)  Small, potent, and selective diaryl phosphonate inhibitors for urokinase-type plasminogen activator with in vivo antimetastatic properties.,  50  (26): [PMID:18052026] [10.1021/jm700962j]

4. 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]

5. 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