ID: ALA468935

Max Phase: Preclinical

Molecular Formula: C17H22N4O3S

Molecular Weight: 362.46

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1cccc(-c2csc(NC(=O)CCCCCCC(=O)NO)n2)c1

Standard InChI:  InChI=1S/C17H22N4O3S/c18-13-7-5-6-12(10-13)14-11-25-17(19-14)20-15(22)8-3-1-2-4-9-16(23)21-24/h5-7,10-11,24H,1-4,8-9,18H2,(H,21,23)(H,19,20,22)

Standard InChI Key:  DRRQFLRBTKPRMM-UHFFFAOYSA-N

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

Properties

Molecular Weight: 362.46

Molecular Weight (Monoisotopic): 362.1413

AlogP: 3.18

#Rotatable Bonds: 9

Polar Surface Area: 117.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.92

CX Basic pKa: 3.55

CX LogP: 2.55

CX LogD: 2.44

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.24

Np Likeness Score: -1.30

References

1. Tapadar S, He R, Luchini DN, Billadeau DD, Kozikowski AP..  (2009)  Isoxazole moiety in the linker region of HDAC inhibitors adjacent to the Zn-chelating group: effects on HDAC biology and antiproliferative activity.,  19  (11): [PMID:19419863] [10.1016/j.bmcl.2009.04.058]

2. Agbor-Enoh S, Seudieu C, Davidson E, Dritschilo A, Jung M..  (2009)  Novel inhibitor of Plasmodium histone deacetylase that cures P. berghei-infected mice.,  53  (5): [PMID:19223622] [10.1128/aac.00729-08]

3. Dow GS, Chen Y, Andrews KT, Caridha D, Gerena L, Gettayacamin M, Johnson J, Li Q, Melendez V, Obaldia N, Tran TN, Kozikowski AP..  (2008)  Antimalarial activity of phenylthiazolyl-bearing hydroxamate-based histone deacetylase inhibitors.,  52  (10): [PMID:18644969] [10.1128/aac.00439-08]

4. Hansen FK, Sumanadasa SD, Stenzel K, Duffy S, Meister S, Marek L, Schmetter R, Kuna K, Hamacher A, Mordmüller B, Kassack MU, Winzeler EA, Avery VM, Andrews KT, Kurz T..  (2014)  Discovery of HDAC inhibitors with potent activity against multiple malaria parasite life cycle stages.,  82  [PMID:24904967] [10.1016/j.ejmech.2014.05.050]

5.  (2010)  Isoform Selective HDAC Inhibitors, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data