3-Amino-5-(azepan-1-yl)-6-(benzofuran-2-yl)-N-carbamimidoylpyrazine-2-carboxamide

ID: ALA4213248

Chembl Id: CHEMBL4213248

PubChem CID: 135393470

Max Phase: Preclinical

Molecular Formula: C20H23N7O2

Molecular Weight: 393.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NC(=O)c1nc(-c2cc3ccccc3o2)c(N2CCCCCC2)nc1N

Standard InChI:  InChI=1S/C20H23N7O2/c21-17-16(19(28)26-20(22)23)24-15(14-11-12-7-3-4-8-13(12)29-14)18(25-17)27-9-5-1-2-6-10-27/h3-4,7-8,11H,1-2,5-6,9-10H2,(H2,21,25)(H4,22,23,26,28)

Standard InChI Key:  FSPGYSVEHLETQR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4213248

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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: 393.45

Molecular Weight (Monoisotopic): 393.1913

AlogP: 2.48

#Rotatable Bonds: 3

Polar Surface Area: 147.15

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.74

CX Basic pKa: 6.13

CX LogP: 3.02

CX LogD: 3.00

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -0.43

References

1. Buckley BJ, Aboelela A, Minaei E, Jiang LX, Xu Z, Ali U, Fildes K, Cheung CY, Cook SM, Johnson DC, Bachovchin DA, Cook GM, Apte M, Huang M, Ranson M, Kelso MJ..  (2018)  6-Substituted Hexamethylene Amiloride (HMA) Derivatives as Potent and Selective Inhibitors of the Human Urokinase Plasminogen Activator for Use in Cancer.,  61  (18): [PMID:30130401] [10.1021/acs.jmedchem.8b00838]

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