2-(2-Imino-4,5,6,7-tetrahydro-benzothiazol-3-yl)-1-p-tolyl-ethanone

ID: ALA198759

Chembl Id: CHEMBL198759

Cas Number: 206983-57-5

PubChem CID: 4817

Max Phase: Preclinical

Molecular Formula: C16H18N2OS

Molecular Weight: 286.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pifithrin-Alpha | pifithrin|206983-57-5|CHEMBL198759|2-(2-Imino-4,5,6,7-tetrahydrobenzo[d]thiazol-3(2H)-yl)-1-(p-tolyl)ethanone|Pifithrin-.alpha.|2-(2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethanone|Tocris-1267|BSPBio_001026|CBDivE_001116|KBioGR_000366|KBioSS_000366|SCHEMBL158627|BCBcMAP01_000143|CHEBI:93168|KBio2_000366|KBio2_002934|KBio2_005502|KBio3_000711|KBio3_000712|OLTZHXYLLRJLST-UHFFFAOYSA-N|Bio1_000477|Bio1_000966|Bio1_001455|Bio2_000353|Bio2_000833|HMS1362D07Show More⌵

Synonyms from Alternative Forms(1): Pifithrin-Alpha

Canonical SMILES:  Cc1ccc(C(=O)Cn2c3c(sc2=N)CCCC3)cc1

Standard InChI:  InChI=1S/C16H18N2OS/c1-11-6-8-12(9-7-11)14(19)10-18-13-4-2-3-5-15(13)20-16(18)17/h6-9,17H,2-5,10H2,1H3

Standard InChI Key:  OLTZHXYLLRJLST-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA198759

   Pifithrin

2. Alternative Forms:

   

   ALA198759

   Pifithrin-α (PFTα)

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: 286.40

Molecular Weight (Monoisotopic): 286.1140

AlogP: 3.10

#Rotatable Bonds: 3

Polar Surface Area: 45.85

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.13

CX Basic pKa: 8.84

CX LogP: 3.56

CX LogD: 2.15

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.87

Np Likeness Score: -1.43

References

1. Barchéchath SD, Tawatao RI, Corr M, Carson DA, Cottam HB..  (2005)  Inhibitors of apoptosis in lymphocytes: synthesis and biological evaluation of compounds related to pifithrin-alpha.,  48  (20): [PMID:16190767] [10.1021/jm0502034]

2. Auld DS, Southall NT, Jadhav A, Johnson RL, Diller DJ, Simeonov A, Austin CP, Inglese J..  (2008)  Characterization of chemical libraries for luciferase inhibitory activity.,  51  (8): [PMID:18363348] [10.1021/jm701302v]

3. Strom E, Sathe S, Komarov PG, Chernova OB, Pavlovska I, Shyshynova I, Bosykh DA, Burdelya LG, Macklis RM, Skaliter R, Komarova EA, Gudkov AV..  (2006)  Small-molecule inhibitor of p53 binding to mitochondria protects mice from gamma radiation.,  2  (9): [PMID:16862141] [10.1038/nchembio809]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Fraunhofer HDAC6