YM-254890

{{Short description|Chemical compound}}

{{Infobox drug

| IUPAC_name = [(1R)-1-[(3S,6S,9S,12S,18R,21S,22R)-21-acetamido-18-benzyl-3-[(1R)-1-methoxyethyl]-4,9,10,12,16,22-hexamethyl-15-methylidene-2,5,8,11,14,17,20-heptaoxo-1,19-dioxa-4,7,10,13,16-pentazacyclodocos-6-yl]-2-methylpropyl] (2S,3R)-2-acetamido-3-hydroxy-4-methylpentanoate

| image = YM-254890_structure.png

| width =

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_CA =

| legal_DE =

| legal_UK =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 568580-02-9

| UNII =

| ATC_prefix =

| ATC_suffix =

| PubChem = 9919454

| ChemSpiderID = 8095094

| ChEMBL = 4288881

| IUPHAR_ligand = 9335

| C=46 | H=69 | N=7 | O=15

| melting_point =

| smiles = C[C@@H]1[C@@H](C(=O)O[C@@H](C(=O)N(C(=C)C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O1)[C@@H](C)OC)C)[C@@H](C(C)C)OC(=O)[C@H]([C@@H](C(C)C)O)NC(=O)C)C)C)C)C)CC2=CC=CC=C2)NC(=O)C

| StdInChI = 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

| StdInChIKey = QVYLWCAYZGFGNF-WBWCVGBTSA-N

}}

YM-254890 is a macrolide antibiotic derived from Chromobacterium species.{{cite journal | vauthors = Mizuno N, Itoh H | title = Functions and regulatory mechanisms of Gq-signaling pathways | journal = Neuro-Signals | year = 2009 | volume = 17 | issue = 1 | pages = 42–54 | doi = 10.1159/000186689 | pmid = 19212139 | s2cid = 556083 | doi-access = free }}{{cite journal | vauthors = Kamato D, Thach L, Bernard R, Chan V, Zheng W, Kaur H, Brimble M, Osman N, Little PJ | display-authors = 6 | title = Structure, Function, Pharmacology, and Therapeutic Potential of the G Protein, Gα/q,11 | journal = Frontiers in Cardiovascular Medicine | date = 2015 | volume = 2 | pages = 14 | doi = 10.3389/fcvm.2015.00014 | pmid = 26664886 | pmc = 4671355 | doi-access = free }}{{cite journal | vauthors = Kamato D, Mitra P, Davis F, Osman N, Chaplin R, Cabot PJ, Afroz R, Thomas W, Zheng W, Kaur H, Brimble M, Little PJ | display-authors = 6 | title = Ga_q proteins: molecular pharmacology and therapeutic potential | journal = Cellular and Molecular Life Sciences | volume = 74 | issue = 8 | pages = 1379–1390 | date = April 2017 | doi = 10.1007/s00018-016-2405-9 | pmid = 27815595 | s2cid = 253596970 | pmc = 11107756 }}{{cite journal | vauthors = Hermes C, König GM, Crüsemann M | title = The chromodepsins - chemistry, biology and biosynthesis of a selective Gq inhibitor natural product family | journal = Natural Product Reports | volume = 38 | issue = 12 | pages = 2276–2292 | date = December 2021 | doi = 10.1039/D1NP00005E | pmid = 33998635 | s2cid = 234748014 }} It is used as a pharmacological research compound which acts as a selective inhibitor of G_q mediated signalling.{{cite journal | vauthors = Xiong XF, Zhang H, Underwood CR, Harpsøe K, Gardella TJ, Wöldike MF, Mannstadt M, Gloriam DE, Bräuner-Osborne H, Strømgaard K | display-authors = 6 | title = Total synthesis and structure-activity relationship studies of a series of selective G protein inhibitors | journal = Nature Chemistry | volume = 8 | issue = 11 | pages = 1035–1041 | date = November 2016 | doi = 10.1038/nchem.2577 | pmid = 27768111 | pmc = 5559716 | bibcode = 2016NatCh...8.1035X }}{{cite journal | vauthors = Xiong XF, Zhang H, Boesgaard MW, Underwood CR, Bräuner-Osborne H, Strømgaard K | title = Structure-Activity Relationship Studies of the Natural Product G_q/11 Protein Inhibitor YM-254890 | journal = ChemMedChem | volume = 14 | issue = 8 | pages = 865–870 | date = April 2019 | doi = 10.1002/cmdc.201900018 | pmid = 30790465 | s2cid = 73469968 }}{{cite journal | vauthors = Li J, Ge Y, Huang JX, Strømgaard K, Zhang X, Xiong XF | title = Heterotrimeric G Proteins as Therapeutic Targets in Drug Discovery | journal = Journal of Medicinal Chemistry | volume = 63 | issue = 10 | pages = 5013–5030 | date = May 2020 | doi = 10.1021/acs.jmedchem.9b01452 | pmid = 31841625 | s2cid = 209389142 }}{{cite journal | vauthors = Zhang H, Nielsen AL, Strømgaard K | title = Recent achievements in developing selective G_q inhibitors | journal = Medicinal Research Reviews | volume = 40 | issue = 1 | pages = 135–157 | date = January 2020 | doi = 10.1002/med.21598 | pmid = 31218731 | s2cid = 195192483 }}{{cite journal | vauthors = Schlegel JG, Tahoun M, Seidinger A, Voss JH, Kuschak M, Kehraus S, Schneider M, Matthey M, Fleischmann BK, König GM, Wenzel D, Müller CE | display-authors = 6 | title = Macrocyclic Gq Protein Inhibitors FR900359 and/or YM-254890-Fit for Translation? | journal = ACS Pharmacology & Translational Science | volume = 4 | issue = 2 | pages = 888–897 | date = April 2021 | doi = 10.1021/acsptsci.1c00021 | pmid = 33860209 | s2cid = 233258488 | pmc = 8033771 }} However the claimed selectivity for G_q has been disputed.{{cite journal | vauthors = Peng Q, Shen J | title = YM-254890 is a General Inhibitor of G Proteins. | journal = The FASEB Journal | date = 2019 | volume = 33 | issue = S1 | pages = 503.7 | doi = 10.1096/fasebj.2019.33.1_supplement.503.7| doi-access = free | s2cid = 241743171 }}