methyl 1-(diphenoxyphosphoryl)-2-(4-guanidinophenyl)ethylcarbamate

ID: ALA393591

Chembl Id: CHEMBL393591

PubChem CID: 16049247

Max Phase: Preclinical

Molecular Formula: C23H25N4O5P

Molecular Weight: 468.45

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

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

Associated Targets(Human)

PLAU Tchem Urokinase-type plasminogen activator (2016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLAT Tclin Tissue-type plasminogen activator (1057 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLG Tclin Plasminogen (2339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
F2 Tclin Thrombin (11687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
F10 Tclin Coagulation factor X (9693 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (10718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
F2 Thrombin (98 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plg Plasminogen (11 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
F2 Thrombin (10 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plau Urokinase-type plasminogen activator (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plau Urokinase-type plasminogen activator (56 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plg Plasminogen (125 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
clpP ATP-dependent Clp protease proteolytic subunit (247 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 468.45Molecular Weight (Monoisotopic): 468.1563AlogP: 4.57#Rotatable Bonds: 9
Polar Surface Area: 135.76Molecular Species: BASEHBA: 6HBD: 4
#RO5 Violations: HBA (Lipinski): 9HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 13.06CX Basic pKa: 10.01CX LogP: 4.32CX LogD: 2.08
Aromatic Rings: 3Heavy Atoms: 33QED Weighted: 0.21Np 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