Ononetin | CAS#487-49-0 | TRPM3 blocker

MedKoo Cat#: 563139 | Name: Ononetin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ononetin is a TRPM3 channel blocker. Ononetin is a TRPM3 channel blocker. Overnight treatment of NK cells with PregS and ononetin resulted in reduced co-localisation of TRPM3 with PIP(2) and actin in HC.

Chemical Structure

Ononetin

CAS#487-49-0

Theoretical Analysis

MedKoo Cat#: 563139

Name: Ononetin

CAS#: 487-49-0

Chemical Formula: C15H14O4

Exact Mass: 258.0892

Molecular Weight: 258.27

Elemental Analysis: C, 69.76; H, 5.46; O, 24.78

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 510.00

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Related CAS #

No Data

Synonym

Ononetin;

IUPAC/Chemical Name

1-(2,4-Dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone

InChi Key

XHBZOAYMBBUURD-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H14O4/c1-19-12-5-2-10(3-6-12)8-14(17)13-7-4-11(16)9-15(13)18/h2-7,9,16,18H,8H2,1H3

SMILES Code

COC1=CC=C(CC(C2=CC=C(O)C=C2O)=O)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ononetin, a natural deoxybenzoin, is a potent and selective TRPM3 channel blocker with an IC50 of 0.3 μM.

In vitro activity:

TBD

In vivo activity:

Intraplantar injections of EP2 or BK2 agonists inhibited both the nocifensive response evoked by TRPM3 agonists, and the heat hypersensitivity produced by Freund's Complete Adjuvant (FCA). Furthermore, FCA-induced heat hypersensitivity was completely reversed by the selective TRPM3 antagonist ononetin in WT mice and did not develop in Trpm3-/- mice. These results demonstrate that TRPM3 is subject to promiscuous inhibition by Gβγ protein in heterologous expression systems, primary neurons and in vivo, and suggest a critical role for this ion channel in inflammatory heat hypersensitivity. Reference: J Neurosci. 2019 Oct 2;39(40):7840-7852. https://pubmed.ncbi.nlm.nih.gov/31451581/

	Solvent	mg/mL	mM
Solubility
	DMF	12.0	46.46
	DMSO	45.9	177.89
	Ethanol	18.9	73.24
	PBS (pH 7.2)	0.3	0.97

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 258.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

Alkhatib O, da Costa R, Gentry C, Quallo T, Bevan S, Andersson DA. Promiscuous G-Protein-Coupled Receptor Inhibition of Transient Receptor Potential Melastatin 3 Ion Channels by Gβγ Subunits. J Neurosci. 2019 Oct 2;39(40):7840-7852. doi: 10.1523/JNEUROSCI.0882-19.2019. Epub 2019 Aug 26. Erratum in: J Neurosci. 2020 Sep 30;40(40):7778. PMID: 31451581; PMCID: PMC6774412.

In vitro protocol:

TBD

In vivo protocol:

1: Sasso EM, Muraki K, Eaton-Fitch N, Smith P, Jeremijenko A, Griffin P, Marshall-Gradisnik S. Investigation into the restoration of TRPM3 ion channel activity in post-COVID-19 condition: a potential pharmacotherapeutic target. Front Immunol. 2024 May 3;15:1264702. doi: 10.3389/fimmu.2024.1264702. PMID: 38765011; PMCID: PMC11099221. 2: Langen KR, Dantzler HA, de Barcellos-Filho PG, Kline DD. Hypoxia augments TRPM3-mediated calcium influx in vagal sensory neurons. Auton Neurosci. 2023 Jul;247:103095. doi: 10.1016/j.autneu.2023.103095. Epub 2023 Apr 29. PMID: 37146443; PMCID: PMC10330432. 3: Sasso EM, Muraki K, Eaton-Fitch N, Smith P, Lesslar OL, Deed G, Marshall- Gradisnik S. Transient receptor potential melastatin 3 dysfunction in post COVID-19 condition and myalgic encephalomyelitis/chronic fatigue syndrome patients. Mol Med. 2022 Aug 19;28(1):98. doi: 10.1186/s10020-022-00528-y. PMID: 35986236; PMCID: PMC9388968. 4: Eaton-Fitch N, Du Preez S, Cabanas H, Muraki K, Staines D, Marshall-Gradisnik S. Impaired TRPM3-dependent calcium influx and restoration using Naltrexone in natural killer cells of myalgic encephalomyelitis/chronic fatigue syndrome patients. J Transl Med. 2022 Feb 16;20(1):94. doi: 10.1186/s12967-022-03297-8. PMID: 35172836; PMCID: PMC8848670. 5: Cabanas H, Muraki K, Eaton-Fitch N, Staines DR, Marshall-Gradisnik S. Potential Therapeutic Benefit of Low Dose Naltrexone in Myalgic Encephalomyelitis/Chronic Fatigue Syndrome: Role of Transient Receptor Potential Melastatin 3 Ion Channels in Pathophysiology and Treatment. Front Immunol. 2021 Jul 13;12:687806. doi: 10.3389/fimmu.2021.687806. PMID: 34326841; PMCID: PMC8313851. 6: Eaton-Fitch N, Cabanas H, du Preez S, Staines D, Marshall-Gradisnik S. The effect of IL-2 stimulation and treatment of TRPM3 on channel co-localisation with PIP2 and NK cell function in myalgic encephalomyelitis/chronic fatigue syndrome patients. J Transl Med. 2021 Jul 15;19(1):306. doi: 10.1186/s12967-021-02974-4. PMID: 34266470; PMCID: PMC8281618. 7: Wei H, Chen Z, Koivisto A, Pertovaara A. Spinal mechanisms contributing to the development of pain hypersensitivity induced by sphingolipids in the rat. Pharmacol Rep. 2021 Apr;73(2):672-679. doi: 10.1007/s43440-020-00207-x. Epub 2021 Jan 3. PMID: 33389723; PMCID: PMC7994220. 8: Cabanas H, Muraki K, Staines D, Marshall-Gradisnik S. Naltrexone Restores Impaired Transient Receptor Potential Melastatin 3 Ion Channel Function in Natural Killer Cells From Myalgic Encephalomyelitis/Chronic Fatigue Syndrome Patients. Front Immunol. 2019 Oct 31;10:2545. doi: 10.3389/fimmu.2019.02545. PMID: 31736966; PMCID: PMC6834647. 9: Alkhatib O, da Costa R, Gentry C, Quallo T, Bevan S, Andersson DA. Promiscuous G-Protein-Coupled Receptor Inhibition of Transient Receptor Potential Melastatin 3 Ion Channels by Gβγ Subunits. J Neurosci. 2019 Oct 2;39(40):7840-7852. doi: 10.1523/JNEUROSCI.0882-19.2019. Epub 2019 Aug 26. Erratum in: J Neurosci. 2020 Sep 30;40(40):7778. doi: 10.1523/JNEUROSCI.2056-20.2020. PMID: 31451581; PMCID: PMC6774412. 10: Cabanas H, Muraki K, Balinas C, Eaton-Fitch N, Staines D, Marshall-Gradisnik S. Validation of impaired Transient Receptor Potential Melastatin 3 ion channel activity in natural killer cells from Chronic Fatigue Syndrome/ Myalgic Encephalomyelitis patients. Mol Med. 2019 Apr 23;25(1):14. doi: 10.1186/s10020-019-0083-4. PMID: 31014226; PMCID: PMC6480905. 11: Cabanas H, Muraki K, Eaton N, Balinas C, Staines D, Marshall-Gradisnik S. Loss of Transient Receptor Potential Melastatin 3 ion channel function in natural killer cells from Chronic Fatigue Syndrome/Myalgic Encephalomyelitis patients. Mol Med. 2018 Aug 14;24(1):44. doi: 10.1186/s10020-018-0046-1. PMID: 30134818; PMCID: PMC6092868. 12: Son GY, Yang YM, Park WS, Chang I, Shin DM. Hypotonic stress induces RANKL via transient receptor potential melastatin 3 (TRPM3) and vaniloid 4 (TRPV4) in human PDL cells. J Dent Res. 2015 Mar;94(3):473-81. doi: 10.1177/0022034514567196. Epub 2015 Jan 16. PMID: 25595364; PMCID: PMC4814022. 13: Straub I, Krügel U, Mohr F, Teichert J, Rizun O, Konrad M, Oberwinkler J, Schaefer M. Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo. Mol Pharmacol. 2013 Nov;84(5):736-50. doi: 10.1124/mol.113.086843. Epub 2013 Sep 4. PMID: 24006495. 14: Straub I, Mohr F, Stab J, Konrad M, Philipp SE, Oberwinkler J, Schaefer M. Citrus fruit and fabacea secondary metabolites potently and selectively block TRPM3. Br J Pharmacol. 2013 Apr;168(8):1835-50. doi: 10.1111/bph.12076. PMID: 23190005; PMCID: PMC3623054.