N-(3-(2-amino-1H-imidazol-4-yl)allyl)-5-fluoro-1H-indole-2-carboxamide

ID: ALA3261431

Chembl Id: CHEMBL3261431

PubChem CID: 90675943

Max Phase: Preclinical

Molecular Formula: C15H14FN5O

Molecular Weight: 299.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(/C=C/CNC(=O)c2cc3cc(F)ccc3[nH]2)c[nH]1

Standard InChI:  InChI=1S/C15H14FN5O/c16-10-3-4-12-9(6-10)7-13(21-12)14(22)18-5-1-2-11-8-19-15(17)20-11/h1-4,6-8,21H,5H2,(H,18,22)(H3,17,19,20)/b2-1+

Standard InChI Key:  HFMHYLCYABPWMX-OWOJBTEDSA-N

Alternative Forms

1. Parent:

   

   ALA3261431

   N-[(E)-3-(2-amino-1H-imidazol-5-yl)prop-2-enyl]-5-fluoro-1H-indole-2-carboxamide

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: 299.31

Molecular Weight (Monoisotopic): 299.1182

AlogP: 2.06

#Rotatable Bonds: 4

Polar Surface Area: 99.59

Molecular Species: BASE

HBA: 3

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.52

CX LogP: 1.51

CX LogD: 0.50

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.59

Np Likeness Score: -0.44

References

1. Hodnik Ž, Łoś JM, Žula A, Zidar N, Jakopin Ž, Łoś M, Sollner Dolenc M, Ilaš J, Węgrzyn G, Peterlin Mašič L, Kikelj D..  (2014)  Inhibition of biofilm formation by conformationally constrained indole-based analogues of the marine alkaloid oroidin.,  24  (11): [PMID:24755428] [10.1016/j.bmcl.2014.03.094]

2. Tomasic T, Nabergoj D, Vrbek S, Zidar N, Jakopin Z, Zula A, Hodnik Z, Jukic M, Anderluh M, Ilas J, Dolenc MS, Peluso J, Ubeaud-Sequier G, Muller CD, Masic LP, Kikelj D.  (2015)  Analogues of the marine alkaloids oroidin, clathrodin, and hymenidin induce apoptosis in human HepG2 and THP-1 cancer cells,  6  (1): [10.1039/C4MD00286E]

3. Zidar N, Žula A, Tomašič T, Rogers M, Kirby RW, Tytgat J, Peigneur S, Kikelj D, Ilaš J, Mašič LP..  (2017)  Clathrodin, hymenidin and oroidin, and their synthetic analogues as inhibitors of the voltage-gated potassium channels.,  139  [PMID:28802123] [10.1016/j.ejmech.2017.08.015]

Source

Source(1):

• Scientific Literature