ID: ALA393591

Max Phase: Preclinical

Molecular Formula: C23H25N4O5P

Molecular Weight: 468.45

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)NC(Cc1ccc(NC(=N)N)cc1)P(=O)(Oc1ccccc1)Oc1ccccc1

Standard InChI:  InChI=1S/C23H25N4O5P/c1-30-23(28)27-21(16-17-12-14-18(15-13-17)26-22(24)25)33(29,31-19-8-4-2-5-9-19)32-20-10-6-3-7-11-20/h2-15,21H,16H2,1H3,(H,27,28)(H4,24,25,26)

Standard InChI Key:  MQQUIUGJIRPZPV-UHFFFAOYSA-N

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

Properties

Molecular Weight: 468.45

Molecular Weight (Monoisotopic): 468.1563

AlogP: 4.57

#Rotatable Bonds: 9

Polar Surface Area: 135.76

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.06

CX Basic pKa: 10.01

CX LogP: 4.32

CX LogD: 2.08

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -0.34

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. 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