Teleocidin B4   Click here for help

GtoPdb Ligand ID: 13408

Synonyms: Olivoretin D | Tel B | Teleocidin B-4
Compound class: Natural product
Comment: Teleocidin B4 is produced by Streptomyces sp. bacteria and other actinomycetes. It was reported to upregulate expression of hypoxia-inducible factor 1 (HIF-1)-responsive genes via activation of protein kinase C α (PKCα) and downstream elevation of HIF-1α expression [1]. Direct binding of a semisynthetic Teleocidin B4 analogue (C38OX6; that differs by only one hydroxymethyl group) to the diacylglycerol binding site of PKCα has previously been reported (Kd 1.1 nM) [2]. This PKCα-HIF-1 activation mechanism is suggested as an approach to reduce ischemia/reperfusion tissue damage.
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 3
Rotatable bonds 4
Topological polar surface area 64.6
Molecular weight 451.65
XLogP 6.24
No. Lipinski's rules broken 1

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 C=C[C@@]1(C)CC[C@](C)(C(C)C)C2=C1C3=C4C(=CN3)C[C@@H](CO)NC(=O)[C@H](C(C)C)N(C)C4=C2
Isomeric SMILES CC(C)[C@H]1C(=O)N[C@@H](CC2=CNC3=C4C(=CC(=C23)N1C)[C@@](CC[C@]4(C)C=C)(C)C(C)C)CO
InChI InChI=1S/C28H41N3O2/c1-9-27(6)10-11-28(7,17(4)5)20-13-21-22-18(14-29-24(22)23(20)27)12-19(15-32)30-26(33)25(16(2)3)31(21)8/h9,13-14,16-17,19,25,29,32H,1,10-12,15H2,2-8H3,(H,30,33)/t19-,25-,27-,28+/m0/s1
InChI Key PEYTUVXFLCCGCC-YGHSORLUSA-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. Iseki S, Ikeda H, Kobayashi S, Irie K, Harada H, Kakeya H. (2024)
Teleocidin B-4, a PKC Activator, Upregulates Hypoxia-Inducible Factor 1 (HIF-1) Activity by Promoting the Accumulation of HIF-1α Protein via the PKCα/mTORC Signaling Pathway.
J Nat Prod, [Epub ahead of print]. DOI: 10.1021/acs.jnatprod.4c00395
2. Kawamura T, Matsubara K, Otaka H, Tashiro E, Shindo K, Yanagita RC, Irie K, Imoto M. (2011)
Generation of 'Unnatural Natural Product' library and identification of a small molecule inhibitor of XIAP.
Bioorg Med Chem, 19 (14): 4377-85. [PMID:21696964]