3,5-diamino-N-carbamimidoyl-6-(2,3-dihydrobenzofuran-5-yl)pyrazine-2-carboxamide

ID: ALA4551391

PubChem CID: 155554981

Max Phase: Preclinical

Molecular Formula: C14H15N7O2

Molecular Weight: 313.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)NC(=O)c1nc(-c2ccc3c(c2)CCO3)c(N)nc1N

Standard InChI:  InChI=1S/C14H15N7O2/c15-11-9(7-1-2-8-6(5-7)3-4-23-8)19-10(12(16)20-11)13(22)21-14(17)18/h1-2,5H,3-4H2,(H4,15,16,20)(H4,17,18,21,22)

Standard InChI Key:  MEKRPVRSPDMWOU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    6.8787  -20.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8775  -21.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5856  -22.1164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2952  -21.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2924  -20.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5838  -20.4790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0036  -22.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695  -22.1154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9986  -20.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7078  -20.8789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9955  -19.6558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4140  -20.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1232  -20.8736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4109  -19.6505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1729  -20.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750  -19.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7646  -20.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4701  -20.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7627  -19.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676  -19.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2975  -18.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4873  -18.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569  -19.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  2  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  1 15  1  0
 15 16  2  0
 16 20  1  0
 19 17  1  0
 17 18  2  0
 18 15  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4551391

   ---

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

Calculated Properties

Molecular Weight: 313.32

Molecular Weight (Monoisotopic): 313.1287

AlogP: -0.13

#Rotatable Bonds: 2

Polar Surface Area: 166.02

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.86

CX Basic pKa: 6.39

CX LogP: 0.60

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.38

Np Likeness Score: -0.33

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]

Source

Source(1):

• Scientific Literature