diphenyl N-(benzyloxycarbonylamino)-(3-guanidinopropyl)-methanephosphonate

ID: ALA239331

Chembl Id: CHEMBL239331

PubChem CID: 44436704

Max Phase: Preclinical

Molecular Formula: C25H29N4O5P

Molecular Weight: 496.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCCC(NC(=O)OCc1ccccc1)P(=O)(Oc1ccccc1)Oc1ccccc1

Standard InChI:  InChI=1S/C25H29N4O5P/c26-24(27)28-18-10-17-23(29-25(30)32-19-20-11-4-1-5-12-20)35(31,33-21-13-6-2-7-14-21)34-22-15-8-3-9-16-22/h1-9,11-16,23H,10,17-19H2,(H,29,30)(H4,26,27,28)

Standard InChI Key:  IVGMDANEFALECQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA239331

   diphenyl N-(benzyloxycarbonylamino)-(3-guanidinopropyl)-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: 496.50

Molecular Weight (Monoisotopic): 496.1876

AlogP: 4.85

#Rotatable Bonds: 12

Polar Surface Area: 135.76

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.16

CX Basic pKa: 11.86

CX LogP: 4.33

CX LogD: 2.08

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.12

Np Likeness Score: -0.11

References

1. 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]

2. 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]

3. 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