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MedKoo Cat#: 145177 | Name: VUAA1

Description:

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

VUAA1 is a synthetic Orco agonist. VUAA1 is reported to be an odorant receptor co-receptor (Orco) agonist in insects with potential use as an insect repellent. VUAA1 presents low toxicity, similar to other insect repellents. VUAA1 is able to activate both heteromeric and homomeric Orco-containing channels.

Chemical Structure

VUAA1
VUAA1
CAS#525582-84-7

Theoretical Analysis

MedKoo Cat#: 145177

Name: VUAA1

CAS#: 525582-84-7

Chemical Formula: C19H21N5OS

Exact Mass: 367.1467

Molecular Weight: 367.47

Elemental Analysis: C, 62.10; H, 5.76; N, 19.06; O, 4.35; S, 8.72

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
VUAA1;
IUPAC/Chemical Name
2-((4-ethyl-5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl)thio)-N-(4-ethylphenyl)acetamide
InChi Key
UWCCKVJVOHTHAF-UHFFFAOYSA-N
InChi Code
1S/C19H21N5OS/c1-3-14-7-9-16(10-8-14)21-17(25)13-26-19-23-22-18(24(19)4-2)15-6-5-11-20-12-15/h5-12H,3-4,13H2,1-2H3,(H,21,25)
SMILES Code
CCN1C(SCC(=O)NC2=CC=C(CC)C=C2)=NN=C1C3=CN=CC=C3
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 367.47 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.

Recalculate based on batch purity %
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
1: Yang L, Demares F, Norris EJ, Jiang S, Bernier UR, Bloomquist JR. Bioactivities and modes of action of VUAA1. Pest Manag Sci. 2021 Aug;77(8):3685-3692. doi: 10.1002/ps.6023. Epub 2020 Aug 25. PMID: 32741076. 2: Corcoran JA, Sonntag Y, Andersson MN, Johanson U, Löfstedt C. Endogenous insensitivity to the Orco agonist VUAA1 reveals novel olfactory receptor complex properties in the specialist fly Mayetiola destructor. Sci Rep. 2018 Feb 22;8(1):3489. doi: 10.1038/s41598-018-21631-3. PMID: 29472565; PMCID: PMC5823858. 3: Kumar BN, Taylor RW, Pask GM, Zwiebel LJ, Newcomb RD, Christie DL. A conserved aspartic acid is important for agonist (VUAA1) and odorant/tuning receptor-dependent activation of the insect odorant co-receptor (Orco). PLoS One. 2013 Jul 23;8(7):e70218. doi: 10.1371/journal.pone.0070218. PMID: 23894621; PMCID: PMC3720905. 4: Jain K, Lavista-Llanos S, Grabe V, Hansson BS, Wicher D. Calmodulin regulates the olfactory performance in Drosophila melanogaster. Sci Rep. 2021 Feb 12;11(1):3747. doi: 10.1038/s41598-021-83296-9. PMID: 33580172; PMCID: PMC7881240. 5: Jones PL, Pask GM, Romaine IM, Taylor RW, Reid PR, Waterson AG, Sulikowski GA, Zwiebel LJ. Allosteric antagonism of insect odorant receptor ion channels. PLoS One. 2012;7(1):e30304. doi: 10.1371/journal.pone.0030304. Epub 2012 Jan 17. PMID: 22272331; PMCID: PMC3260273. 6: Mukunda L, Miazzi F, Kaltofen S, Hansson BS, Wicher D. Calmodulin modulates insect odorant receptor function. Cell Calcium. 2014 Apr;55(4):191-9. doi: 10.1016/j.ceca.2014.02.013. Epub 2014 Feb 23. PMID: 24661599. 7: Mukunda L, Lavista-Llanos S, Hansson BS, Wicher D. Dimerisation of the Drosophila odorant coreceptor Orco. Front Cell Neurosci. 2014 Aug 28;8:261. doi: 10.3389/fncel.2014.00261. PMID: 25221476; PMCID: PMC4147393. 8: Miazzi F, Hansson BS, Wicher D. Odor-induced cAMP production in Drosophila melanogaster olfactory sensory neurons. J Exp Biol. 2016 Jun 15;219(Pt 12):1798-803. doi: 10.1242/jeb.137901. Epub 2016 Apr 4. PMID: 27045092. 9: Guo L, Zhao H, Jiang Y. Expressional and functional interactions of two Apis cerana cerana olfactory receptors. PeerJ. 2018 Jun 11;6:e5005. doi: 10.7717/peerj.5005. PMID: 29910990; PMCID: PMC6001824. 10: Turner RM, Derryberry SL, Kumar BN, Brittain T, Zwiebel LJ, Newcomb RD, Christie DL. Mutational analysis of cysteine residues of the insect odorant co- receptor (Orco) from Drosophila melanogaster reveals differential effects on agonist- and odorant-tuning receptor-dependent activation. J Biol Chem. 2014 Nov 14;289(46):31837-31845. doi: 10.1074/jbc.M114.603993. Epub 2014 Sep 30. PMID: 25271160; PMCID: PMC4231661. 11: Pacalon J, Audic G, Magnat J, Philip M, Golebiowski J, Moreau CJ, Topin J. Elucidation of the structural basis for ligand binding and translocation in conserved insect odorant receptor co-receptors. Nat Commun. 2023 Dec 11;14(1):8182. doi: 10.1038/s41467-023-44058-5. Erratum in: Nat Commun. 2024 May 23;15(1):4398. doi: 10.1038/s41467-024-48896-9. PMID: 38081900; PMCID: PMC10713630. 12: Chen S, Luetje CW. Identification of new agonists and antagonists of the insect odorant receptor co-receptor subunit. PLoS One. 2012;7(5):e36784. doi: 10.1371/journal.pone.0036784. Epub 2012 May 8. PMID: 22590607; PMCID: PMC3348135. 13: Jones PL, Pask GM, Rinker DC, Zwiebel LJ. Functional agonism of insect odorant receptor ion channels. Proc Natl Acad Sci U S A. 2011 May 24;108(21):8821-5. doi: 10.1073/pnas.1102425108. Epub 2011 May 9. Erratum in: Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):11298. PMID: 21555561; PMCID: PMC3102409. 14: Taylor RW, Romaine IM, Liu C, Murthi P, Jones PL, Waterson AG, Sulikowski GA, Zwiebel LJ. Structure-activity relationship of a broad-spectrum insect odorant receptor agonist. ACS Chem Biol. 2012 Oct 19;7(10):1647-52. doi: 10.1021/cb300331z. Epub 2012 Aug 27. PMID: 22924767. 15: Pask GM, Bobkov YV, Corey EA, Ache BW, Zwiebel LJ. Blockade of insect odorant receptor currents by amiloride derivatives. Chem Senses. 2013 Mar;38(3):221-9. doi: 10.1093/chemse/bjs100. Epub 2013 Jan 4. PMID: 23292750; PMCID: PMC3569625. 16: Bobkov Y, Corey E, Ache B. An inhibitor of Na(+)/Ca(2+) exchange blocks activation of insect olfactory receptors. Biochem Biophys Res Commun. 2014 Jul 25;450(2):1104-9. doi: 10.1016/j.bbrc.2014.06.120. Epub 2014 Jul 1. PMID: 24996179; PMCID: PMC4112011. 17: Cattaneo AM, Gonzalez F, Bengtsson JM, Corey EA, Jacquin-Joly E, Montagné N, Salvagnin U, Walker WB, Witzgall P, Anfora G, Bobkov YV. Candidate pheromone receptors of codling moth Cydia pomonella respond to pheromones and kairomones. Sci Rep. 2017 Jan 24;7:41105. doi: 10.1038/srep41105. PMID: 28117454; PMCID: PMC5259778. 18: Roberts RE, Yuvaraj JK, Andersson MN. Codon Optimization of Insect Odorant Receptor Genes May Increase Their Stable Expression for Functional Characterization in HEK293 Cells. Front Cell Neurosci. 2021 Sep 6;15:744401. doi: 10.3389/fncel.2021.744401. PMID: 34552471; PMCID: PMC8450354. 19: Nolte A, Funk NW, Mukunda L, Gawalek P, Werckenthin A, Hansson BS, Wicher D, Stengl M. In situ tip-recordings found no evidence for an Orco-based ionotropic mechanism of pheromone-transduction in Manduca sexta. PLoS One. 2013 May 3;8(5):e62648. doi: 10.1371/journal.pone.0062648. PMID: 23671617; PMCID: PMC3643954. 20: Bobkov YV, Walker Iii WB, Cattaneo AM. Altered functional properties of the codling moth Orco mutagenized in the intracellular loop-3. Sci Rep. 2021 Feb 16;11(1):3893. doi: 10.1038/s41598-021-83024-3. PMID: 33594162; PMCID: PMC7887336.