YM-254890
featured

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

Hodoodo CAT#: H565455

CAS#: 568580-02-9

Description: YM-254890 is a novel gαq/11-selective inhibitor, inhibiting adp-induced platelet aggregation and blocking gαq/11-coupled adp receptor p2y1-mediated ca2+ mobilization.


Chemical Structure

img
YM-254890
CAS# 568580-02-9

Theoretical Analysis

Hodoodo Cat#: H565455
Name: YM-254890
CAS#: 568580-02-9
Chemical Formula: C46H69N7O15
Exact Mass: 959.49
Molecular Weight: 960.092
Elemental Analysis: C, 57.55; H, 7.24; N, 10.21; O, 25.00

Price and Availability

Size Price Availability Quantity
1mg USD 650 2 Weeks
Bulk inquiry

Synonym: YM 254890; YM254890; YM-254890; QS-3666A; QS3666A; QS 3666A;

IUPAC/Chemical Name: (R)-1-((3S,6S,9S,12S,18R,21S,22R)-21-Acetamido-18-benzyl-3-((R)-1-methoxyethyl)-4,9,10,12,16,22-hexamethyl-15-methylene-2,5,8,11,14,17,20-heptaoxo-1,19-dioxa-4,7,10,13,16-pentaazacyclodocosan-6-yl)-2-methylpropyl (2S,3R)-2-acetamido-3-hydroxy-4-methylpentanoate

InChi Key: QVYLWCAYZGFGNF-WBWCVGBTSA-N

InChi Code: InChI=1S/C46H69N7O15/c1-22(2)37(56)34(49-30(11)55)45(63)68-38(23(3)4)35-43(61)53(14)36(28(9)65-15)46(64)66-27(8)33(48-29(10)54)44(62)67-32(21-31-19-17-16-18-20-31)42(60)52(13)25(6)39(57)47-24(5)41(59)51(12)26(7)40(58)50-35/h16-20,22-24,26-28,32-38,56H,6,21H2,1-5,7-15H3,(H,47,57)(H,48,54)(H,49,55)(H,50,58)/t24-,26-,27+,28+,32+,33-,34-,35-,36-,37+,38+/m0/s1

SMILES Code: CC(C)[C@@H](O)[C@H](NC(C)=O)C(O[C@@H]([C@H](NC([C@H](C)N(C)C([C@H](C)NC(C(N(C)C([C@@H](CC1=CC=CC=C1)O2)=O)=C)=O)=O)=O)C(N(C)[C@@H]([C@H](OC)C)C(O[C@H](C)[C@H](NC(C)=O)C2=O)=O)=O)C(C)C)=O

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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 960.09 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Zhang H, Nielsen AL, Strømgaard K. Recent achievements in developing selective G(q) inhibitors. Med Res Rev. 2019 Jun 19. doi: 10.1002/med.21598. [Epub ahead of print] Review. PubMed PMID: 31218731.

2: Mun HC, Leach KM, Conigrave AD. L-Amino Acids Promote Calcitonin Release via a Calcium-Sensing Receptor: Gq/11-Mediated Pathway in Human C-Cells. Endocrinology. 2019 Jul 1;160(7):1590-1599. doi: 10.1210/en.2018-00860. PubMed PMID: 31127815.

3: Xiong XF, Zhang H, Boesgaard MW, Underwood CR, Bräuner-Osborne H, Strømgaard K. Structure-Activity Relationship Studies of the Natural Product G(q/11) Protein Inhibitor YM-254890. ChemMedChem. 2019 Apr 17;14(8):865-870. doi: 10.1002/cmdc.201900018. Epub 2019 Mar 21. PubMed PMID: 30790465.

4: Malfacini D, Patt J, Annala S, Harpsøe K, Eryilmaz F, Reher R, Crüsemann M, Hanke W, Zhang H, Tietze D, Gloriam DE, Bräuner-Osborne H, Strømgaard K, König GM, Inoue A, Gomeza J, Kostenis E. Rational design of a heterotrimeric G protein α subunit with artificial inhibitor sensitivity. J Biol Chem. 2019 Apr 12;294(15):5747-5758. doi: 10.1074/jbc.RA118.007250. Epub 2019 Feb 11. PubMed PMID: 30745359; PubMed Central PMCID: PMC6463727.

5: Weng Y, Wang J, Yang Z, Xi M, Duan J, Guo C, Yin Y, Segawa R, Moriya T, Yonezawa T, Cha BY, Woo JT, Wen A, Hirasawa N. A steroid alkaloid derivative 02F04 upregulates thymic stromal lymphopoietin expression slowly and continuously through a novel Gq/11-ROCK-ERK1/2 signaling pathway in mouse keratinocytes. Cell Signal. 2019 May;57:58-64. doi: 10.1016/j.cellsig.2019.01.005. Epub 2019 Jan 19. PubMed PMID: 30664940.

6: Meleka MM, Edwards AJ, Xia J, Dahlen SA, Mohanty I, Medcalf M, Aggarwal S, Moeller KD, Mortensen OV, Osei-Owusu P. Anti-hypertensive mechanisms of cyclic depsipeptide inhibitor ligands for G(q/11) class G proteins. Pharmacol Res. 2019 Mar;141:264-275. doi: 10.1016/j.phrs.2019.01.012. Epub 2019 Jan 10. PubMed PMID: 30634050; PubMed Central PMCID: PMC6417918.

7: Dietze R, Starzinski-Powitz A, Scheiner-Bobis G, Tinneberg HR, Meinhold-Heerlein I, Konrad L. Lysophosphatidic acid triggers cathepsin B-mediated invasiveness of human endometriotic cells. Biochim Biophys Acta Mol Cell Biol Lipids. 2018 Nov;1863(11):1369-1377. doi: 10.1016/j.bbalip.2018.08.013. Epub 2018 Aug 20. PubMed PMID: 30591146.

8: Patelis N, Kakavia K, Maltezos K, Damaskos C, Spartalis E, Matheiken S, Georgopoulos S. An Update on Novel Antiplatelets in Vascular Patients. Curr Pharm Des. 2018;24(38):4558-4563. doi: 10.2174/1381612825666181226144129. PubMed PMID: 30585537.

9: Björling K, Joseph PD, Egebjerg K, Salomonsson M, Hansen JL, Ludvigsen TP, Jensen LJ. Role of age, Rho-kinase 2 expression, and G protein-mediated signaling in the myogenic response in mouse small mesenteric arteries. Physiol Rep. 2018 Sep;6(17):e13863. doi: 10.14814/phy2.13863. PubMed PMID: 30198176; PubMed Central PMCID: PMC6129776.

10: Mårtensson J, Holdfeldt A, Sundqvist M, Gabl M, Kenakin TP, Björkman L, Forsman H, Dahlgren C. Neutrophil priming that turns natural FFA2R agonists into potent activators of the superoxide generating NADPH-oxidase. J Leukoc Biol. 2018 Dec;104(6):1117-1132. doi: 10.1002/JLB.2A0318-130RR. Epub 2018 Aug 22. PubMed PMID: 30134499.

11: Ng PY, McIntosh KA, Hargrave G, Ho KH, Paul A, Plevin R. Inhibition of cytokine-mediated JNK signalling by purinergic P2Y(11) receptors, a novel protective mechanism in endothelial cells. Cell Signal. 2018 Nov;51:59-71. doi: 10.1016/j.cellsig.2018.07.016. Epub 2018 Aug 2. PubMed PMID: 30076967.

12: Zhang H, Nielsen AL, Boesgaard MW, Harpsøe K, Daly NL, Xiong XF, Underwood CR, Haugaard-Kedström LM, Bräuner-Osborne H, Gloriam DE, Strømgaard K. Structure-activity relationship and conformational studies of the natural product cyclic depsipeptides YM-254890 and FR900359. Eur J Med Chem. 2018 Aug 5;156:847-860. doi: 10.1016/j.ejmech.2018.07.023. Epub 2018 Jul 12. PubMed PMID: 30055466.

13: Wang B, Murakami Y, Ono M, Fujikawa S, Matsuyama H, Unno T, Naitou K, Tanahashi Y. Muscarinic suppression of ATP-sensitive K(+) channels mediated by the M(3)/G(q/11)/phospholipase C pathway contributes to mouse ileal smooth muscle contractions. Am J Physiol Gastrointest Liver Physiol. 2018 Oct 1;315(4):G618-G630. doi: 10.1152/ajpgi.00069.2018. Epub 2018 Jul 12. PubMed PMID: 30001145.

14: Matoba A, Matsuyama N, Shibata S, Masaki E, Emala CW Sr, Mizuta K. The free fatty acid receptor 1 promotes airway smooth muscle cell proliferation through MEK/ERK and PI3K/Akt signaling pathways. Am J Physiol Lung Cell Mol Physiol. 2018 Mar 1;314(3):L333-L348. doi: 10.1152/ajplung.00129.2017. Epub 2017 Nov 2. PubMed PMID: 29097424; PubMed Central PMCID: PMC5900353.

15: Grippi C, Izzi B, Gianfagna F, Noro F, Falcinelli E, Di Pardo A, Amico E, Donati MB, de Gaetano G, Iacoviello L, Hoylaerts MF, Cerletti C. Neuromedin U potentiates ADP- and epinephrine-induced human platelet activation. Thromb Res. 2017 Nov;159:100-108. doi: 10.1016/j.thromres.2017.09.027. Epub 2017 Sep 29. PubMed PMID: 29078099.

16: Mizuno N, Abe K, Morishita Y, Yamashita S, Segawa R, Dong J, Moriya T, Hiratsuka M, Hirasawa N. Pentanoic acid induces thymic stromal lymphopoietin production through G(q/11) and Rho-associated protein kinase signaling pathway in keratinocytes. Int Immunopharmacol. 2017 Sep;50:216-223. doi: 10.1016/j.intimp.2017.06.024. Epub 2017 Jul 3. PubMed PMID: 28683366.

17: Zhang H, Xiong XF, Boesgaard MW, Underwood CR, Bräuner-Osborne H, Strømgaard K. Structure-Activity Relationship Studies of the Cyclic Depsipeptide Natural Product YM-254890, Targeting the G(q) Protein. ChemMedChem. 2017 Jun 7;12(11):830-834. doi: 10.1002/cmdc.201700155. Epub 2017 May 16. PubMed PMID: 28509439.

18: Roszko KL, Bi R, Gorvin CM, Bräuner-Osborne H, Xiong XF, Inoue A, Thakker RV, Strømgaard K, Gardella T, Mannstadt M. Knockin mouse with mutant Gα(11) mimics human inherited hypocalcemia and is rescued by pharmacologic inhibitors. JCI Insight. 2017 Feb 9;2(3):e91079. doi: 10.1172/jci.insight.91079. PubMed PMID: 28194446; PubMed Central PMCID: PMC5291736.

19: Kamato D, Mitra P, Davis F, Osman N, Chaplin R, Cabot PJ, Afroz R, Thomas W, Zheng W, Kaur H, Brimble M, Little PJ. Ga(q) proteins: molecular pharmacology and therapeutic potential. Cell Mol Life Sci. 2017 Apr;74(8):1379-1390. doi: 10.1007/s00018-016-2405-9. Epub 2016 Nov 4. Review. PubMed PMID: 27815595.

20: Xiong XF, Zhang H, Underwood CR, Harpsøe K, Gardella TJ, Wöldike MF, Mannstadt M, Gloriam DE, Bräuner-Osborne H, Strømgaard K. Total synthesis and structure-activity relationship studies of a series of selective G protein inhibitors. Nat Chem. 2016 Nov;8(11):1035-1041. doi: 10.1038/nchem.2577. Epub 2016 Jul 25. PubMed PMID: 27768111; PubMed Central PMCID: PMC5559716.