ID: ALA4513418

Max Phase: Preclinical

Molecular Formula: C11H13N9O2

Molecular Weight: 303.29

Molecule Type: Unknown

Representations

Canonical SMILES:  COc1ncc(-c2nc(C(=O)NC(=N)N)c(N)nc2N)cn1

Standard InChI:  InChI=1S/C11H13N9O2/c1-22-11-16-2-4(3-17-11)5-7(12)19-8(13)6(18-5)9(21)20-10(14)15/h2-3H,1H3,(H4,12,13,19)(H4,14,15,20,21)

Standard InChI Key:  XFGYFQDKMRBURI-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 303.29

Molecular Weight (Monoisotopic): 303.1192

AlogP: -1.27

#Rotatable Bonds: 3

Polar Surface Area: 191.80

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.83

CX Basic pKa: 6.54

CX LogP: -0.69

CX LogD: -0.74

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.34

Np Likeness Score: -0.36

References

1. Buckley BJ, Majed H, Aboelela A, Minaei E, Jiang L, Fildes K, Cheung CY, Johnson D, Bachovchin D, Cook GM, Huang M, Ranson M, Kelso MJ..  (2019)  6-Substituted amiloride derivatives as inhibitors of the urokinase-type plasminogen activator for use in metastatic disease.,  29  (24): [PMID:31679971] [10.1016/j.bmcl.2019.126753]

2. Buckley BJ,Aboelela A,Majed H,Bujaroski RS,White KL,Powell AK,Wang W,Katneni K,Saunders J,Shackleford DM,Charman SA,Cook GM,Kelso MJ,Ranson M.  (2021)  Systematic evaluation of structure-property relationships and pharmacokinetics in 6-(hetero)aryl-substituted matched pair analogs of amiloride and 5-(N,N-hexamethylene)amiloride.,  37  [PMID:33799173] [10.1016/j.bmc.2021.116116]

3. S El Salamouni N, Buckley BJ, Jiang L, Huang M, Ranson M, Kelso MJ, Yu H..  (2022)  Disruption of Water Networks is the Cause of Human/Mouse Species Selectivity in Urokinase Plasminogen Activator (uPA) Inhibitors Derived from Hexamethylene Amiloride (HMA).,  65  (3.0): [PMID:34898192] [10.1021/acs.jmedchem.1c01423]

Source

Source(1):

• Scientific Literature