methyl 1-(bis(4-acetamidophenoxy)phosphoryl)-2-(4guanidino-phenyl)ethylcarbamate

ID: ALA393979

Chembl Id: CHEMBL393979

PubChem CID: 16718713

Max Phase: Preclinical

Molecular Formula: C27H31N6O7P

Molecular Weight: 582.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)NC(Cc1ccc(NC(=N)N)cc1)P(=O)(Oc1ccc(NC(C)=O)cc1)Oc1ccc(NC(C)=O)cc1

Standard InChI:  InChI=1S/C27H31N6O7P/c1-17(34)30-20-8-12-23(13-9-20)39-41(37,40-24-14-10-21(11-15-24)31-18(2)35)25(33-27(36)38-3)16-19-4-6-22(7-5-19)32-26(28)29/h4-15,25H,16H2,1-3H3,(H,30,34)(H,31,35)(H,33,36)(H4,28,29,32)

Standard InChI Key:  VYDDQNBUEWMIFT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA393979

   Methyl 1-(bis(4-acetamidophenoxy)phosphoryl)-2-(4guanidino-phenyl)ethylcarbamate

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: 582.55

Molecular Weight (Monoisotopic): 582.1992

AlogP: 4.48

#Rotatable Bonds: 11

Polar Surface Area: 193.96

Molecular Species: BASE

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.72

CX Basic pKa: 10.00

CX LogP: 2.98

CX LogD: 0.74

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.11

Np Likeness Score: -0.30

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]

Source

Source(1):

• Scientific Literature