diphenyl 1-(benzyloxycarbonylamino)-2-(4-guanidinophenyl)-ethanephosphonate

ID: ALA239535

Chembl Id: CHEMBL239535

PubChem CID: 16718808

Max Phase: Preclinical

Molecular Formula: C29H29N4O5P

Molecular Weight: 544.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H29N4O5P/c30-28(31)32-24-18-16-22(17-19-24)20-27(33-29(34)36-21-23-10-4-1-5-11-23)39(35,37-25-12-6-2-7-13-25)38-26-14-8-3-9-15-26/h1-19,27H,20-21H2,(H,33,34)(H4,30,31,32)

Standard InChI Key:  CTDHLROQTKJDLK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA239535

   Diphenyl 1-(benzyloxycarbonylamino)-2-(4-guanidinophenyl)-ethanephosphonate

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: 544.55

Molecular Weight (Monoisotopic): 544.1876

AlogP: 6.14

#Rotatable Bonds: 11

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: 13.11

CX Basic pKa: 10.01

CX LogP: 6.04

CX LogD: 3.80

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.10

Np Likeness Score: -0.31

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]

Source

Source(1):

• Scientific Literature