4-(1-(2-Aminopyrimidin-4-yl)-5-methoxy-1H-indol-6-yl)-2-methylbut-3-yn-2-ol

ID: ALA5280803

Max Phase: Preclinical

Molecular Formula: C18H18N4O2

Molecular Weight: 322.37

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cc2ccn(-c3ccnc(N)n3)c2cc1C#CC(C)(C)O

Standard InChI:  InChI=1S/C18H18N4O2/c1-18(2,23)7-4-13-10-14-12(11-15(13)24-3)6-9-22(14)16-5-8-20-17(19)21-16/h5-6,8-11,23H,1-3H3,(H2,19,20,21)

Standard InChI Key:  VNKYVVIEELPQIE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    6.7769   -9.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1896   -9.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5980   -9.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3663  -12.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760  -11.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0732  -11.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645  -10.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6583  -11.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595  -11.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790  -10.8003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3953  -11.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8770  -12.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6277  -10.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759   -9.4178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9251   -8.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1253   -8.4691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5767   -9.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -9.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7793  -10.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855  -10.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9009  -10.2254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4732   -8.0347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7843  -12.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7856  -13.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 12  8  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  6 19  1  0
 19 20  3  0
 20  2  1  0
  2 21  1  0
 15 22  1  0
 11 12  2  0
  5 23  1  0
 23 24  1  0
M  END

Alternative Forms

  1. Parent:

    ALA5280803

    ---

Associated Targets(Human)

TTBK1 Tbio Tau-tubulin kinase 1 (179 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Topical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 322.37Molecular Weight (Monoisotopic): 322.1430AlogP: 2.13#Rotatable Bonds: 2
Polar Surface Area: 86.19Molecular Species: NEUTRALHBA: 6HBD: 2
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 13.68CX Basic pKa: 6.26CX LogP: 2.72CX LogD: 2.69
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.71Np Likeness Score: -0.53

References

1. Halkina T, Henderson JL, Lin EY, Himmelbauer MK, Jones JH, Nevalainen M, Feng J, King K, Rooney M, Johnson JL, Marcotte DJ, Chodaparambil JV, Kumar PR, Patterson TA, Murugan P, Schuman E, Wong L, Hesson T, Lamore S, Bao C, Calhoun M, Certo H, Amaral B, Dillon GM, Gilfillan R, de Turiso FG..  (2021)  Discovery of Potent and Brain-Penetrant Tau Tubulin Kinase 1 (TTBK1) Inhibitors that Lower Tau Phosphorylation In Vivo.,  64  (9.0): [PMID:33944571] [10.1021/acs.jmedchem.1c00382]

Source