3-Amino-5-(azepan-1-yl)-N-carbamimidoyl-6-(4-(trifluoromethyl)phenyl)pyrazine-2-carboxamide

ID: ALA4203024

Chembl Id: CHEMBL4203024

PubChem CID: 146029518

Max Phase: Preclinical

Molecular Formula: C19H22F3N7O

Molecular Weight: 421.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NC(=O)c1nc(-c2ccc(C(F)(F)F)cc2)c(N2CCCCCC2)nc1N

Standard InChI:  InChI=1S/C19H22F3N7O/c20-19(21,22)12-7-5-11(6-8-12)13-16(29-9-3-1-2-4-10-29)27-15(23)14(26-13)17(30)28-18(24)25/h5-8H,1-4,9-10H2,(H2,23,27)(H4,24,25,28,30)

Standard InChI Key:  DJXOPWDCWQNTGK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4203024

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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: 421.43

Molecular Weight (Monoisotopic): 421.1838

AlogP: 2.75

#Rotatable Bonds: 3

Polar Surface Area: 134.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.83

CX Basic pKa: 6.59

CX LogP: 3.82

CX LogD: 3.76

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: -0.82

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]

Source

Source(1):

• Scientific Literature