teglicar   Click here for help

GtoPdb Ligand ID: 12976

Synonyms: compound 17 [Giannessi et al., 2003] | ST-1326 | ST1326
PDB Ligand
Compound class: Synthetic organic
Comment: Teglicar (ST1326) is a reversible carnitine palmitoyltransferase inhibitor [2]. It is a substrate analogue that mimics palmitoylcarnitine. Teglicar has been investigated for anti-cancer effects in solid [1] and liquid tumours [3-5].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 5
Hydrogen bond donors 2
Rotatable bonds 20
Topological polar surface area 81.26
Molecular weight 399.61
XLogP 5.15
No. Lipinski's rules broken 2

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 CCCCCCCCCCCCCCNC(=O)N[C@H](CC(=O)[O-])C[N+](C)(C)C
Isomeric SMILES CCCCCCCCCCCCCCNC(=O)N[C@H](CC(=O)[O-])C[N+](C)(C)C
InChI InChI=1S/C22H45N3O3/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-23-22(28)24-20(18-21(26)27)19-25(2,3)4/h20H,5-19H2,1-4H3,(H2-,23,24,26,27,28)/t20-/m1/s1
InChI Key BMZYTDRMCBZVNH-HXUWFJFHSA-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. Cacciola NA, Sepe F, Fioriniello S, Petillo O, Margarucci S, Scivicco M, Peluso G, Balestrieri A, Bifulco G, Restucci B et al.. (2023)
The Carnitine Palmitoyltransferase 1A Inhibitor Teglicar Shows Promising Antitumour Activity against Canine Mammary Cancer Cells by Inducing Apoptosis.
Pharmaceuticals (Basel), 16 (7). [PMID:37513899]
2. Giannessi F, Pessotto P, Tassoni E, Chiodi P, Conti R, De Angelis F, Dell'Uomo N, Catini R, Deias R, Tinti MO et al.. (2003)
Discovery of a Long-Chain Carbamoyl Aminocarnitine Derivative, a Reversible Carnitine Palmitoyltransferase Inhibitor with Antiketotic and Antidiabetic Activity.
Jourmal of Medicinal Chemistry, 46 (2): 303–309. DOI: 10.1021/jm020979u
3. Gugiatti E, Tenca C, Ravera S, Fabbi M, Ghiotto F, Mazzarello AN, Bagnara D, Reverberi D, Zarcone D, Cutrona G et al.. (2018)
A reversible carnitine palmitoyltransferase (CPT1) inhibitor offsets the proliferation of chronic lymphocytic leukemia cells.
Haematologica, 103 (11): e531-e536. [PMID:29930162]
4. Pacilli A, Calienni M, Margarucci S, D'Apolito M, Petillo O, Rocchi L, Pasquinelli G, Nicolai R, Koverech A, Calvani M et al.. (2013)
Carnitine-acyltransferase system inhibition, cancer cell death, and prevention of myc-induced lymphomagenesis.
J Natl Cancer Inst, 105 (7): 489-98. [PMID:23486551]
5. Ricciardi MR, Mirabilii S, Allegretti M, Licchetta R, Calarco A, Torrisi MR, Foà R, Nicolai R, Peluso G, Tafuri A. (2015)
Targeting the leukemia cell metabolism by the CPT1a inhibition: functional preclinical effects in leukemias.
Blood, 126 (16): 1925-9. [PMID:26276667]
6. Rufer AC, Lomize A, Benz J, Chomienne O, Thoma R, Hennig M. (2007)
Carnitine palmitoyltransferase 2: analysis of membrane association and complex structure with a substrate analog.
FEBS Lett, 581 (17): 3247-52. [PMID:17585909]
7. Rufer AC, Thoma R, Benz J, Stihle M, Gsell B, De Roo E, Banner DW, Mueller F, Chomienne O, Hennig M. (2006)
The crystal structure of carnitine palmitoyltransferase 2 and implications for diabetes treatment.
Structure, 14 (4): 713-23. [PMID:16615913]