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HT-01   Click here for help

GtoPdb Ligand ID: 14302

Synonyms: compound 35 [PMID: 23103940]
 Ligand is labelled
Compound class: Synthetic organic
Comment: HT-01 is a fluorescent probe (inhibitor) of diacylglycerol lipase β (DAGLβ) and the serine hydrolase ABHD6 [1]. Its chemical structure is derived from the structure of the DAGL inhibitor KT-109 with the addition of a linker and a BODIPY fluorophore.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 18
Topological polar surface area 92.85
Molecular weight 735.56
XLogP 7.31
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1=C2C=C3C=CC(=[N+]3[B-](F)(F)N2C(=C1)C)CCC(=O)NCCCCCN(CCC4=CC=CC=C4)C(=O)N5C=C(C6=CC=C(C=C6)OC(F)(F)F)N=N5
Isomeric SMILES CC1=CC(C)=C2C=C3C=CC(CCC(=O)NCCCCCN(CCC4=CC=CC=C4)C(=O)N5C=C(N=N5)C6=CC=C(OC(F)(F)F)C=C6)=[N+]3[B-](F)(F)N12
InChI InChI=1S/C37H39BF5N7O3/c1-26-23-27(2)49-34(26)24-31-14-13-30(50(31)38(49,42)43)15-18-35(51)44-20-7-4-8-21-47(22-19-28-9-5-3-6-10-28)36(52)48-25-33(45-46-48)29-11-16-32(17-12-29)53-37(39,40)41/h3,5-6,9-14,16-17,23-25H,4,7-8,15,18-22H2,1-2H3,(H,44,51)
InChI Key OWIPXLLGTKENRU-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Hsu KL, Tsuboi K, Adibekian A, Pugh H, Masuda K, Cravatt BF. (2012)
DAGLβ inhibition perturbs a lipid network involved in macrophage inflammatory responses.
Nat Chem Biol, 8 (12): 999-1007. [PMID:23103940]
2. van Rooden EJ, Kohsiek M, Kreekel R, van Esbroeck ACM, van den Nieuwendijk AMCH, Janssen APA, van den Berg RJBHN, Overkleeft HS, van der Stelt M. (2018)
Design and Synthesis of Quenched Activity-based Probes for Diacylglycerol Lipase and α,β-Hydrolase Domain Containing Protein 6.
Chem Asian J, 13 (22): 3491-3500. [PMID:29901868]