657:
93:
36:
232:
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Depicting the process of hydrolysis and biosynthesis at the plasma membrane and
Endoplasmic Reticulum (ER). Describing the cycle of PI, with respective enzymatic processes and reactions. Made by Mathias Sollie Sandsdalen in BioRender.com, modified from N.J.
98:
Depicting the
Phosphatidylinisitol molecule with an overview of different segregated components; Inositol, Phosphate, Glycerol-backbone, sn-1 acyl chain, sn-2 acyl chain. Made by Mathias Sollie Sandsdalen in BioRender.com, modified from N.J. Blunsom and S.
407:
Phosphatidylinositol (PI), also known as inositol phospholipid, is a lipid composed of a phosphate group, two fatty acid chains, and one inositol molecule. It belongs to the class of phosphatidylglycerides and is typically found as a minor component on the cytosolic side of
594:
The significance of phosphatidylinositol (PI) metabolism lies in its role as a potential transducing mechanism, evident from studies showing hormone and neurotransmitter-induced hydrolysis of PI. The hydrolysis starts with the enzyme PI 4-kinase alpha
430:
nature, with both polar and non-polar regions, due to its glycerophospholipid structure containing a glycerol backbone, two non-polar fatty acid tails, and a phosphate group substituted with an inositol polar head group.
395:. From early investigations into inositol's structure to the identification of its various isomers and their physiological functions, the study of inositol compounds continues to uncover new insights into
893:
Posternak, Théodore (1942). "Recherches dans la série des cyclites VI. Sut la configuration de la méso-inosite, de la scyllite et d'un inosose obtenu par voie biochimique (scyllo-ms-inosose)".
735:
649:). Lipid transfer proteins facilitate the exchange of PI and PA between membranes, ensuring its availability for receptor mechanisms on the plasma membrane, even in organelles like
245:
384:. Despite the complexity of inositol nomenclature and isomerism, modern research has greatly advanced the understanding of their diverse functions in cellular physiology and
54:
423:, transcription, mRNA export and translation, insulin signaling, embryonic development and stress response. Cis-inositol is the only isomer not found naturally in nature.
1382:
Inositol
Phospholipid Metabolism in Arabidopsis. Characterized and Putative Isoforms of Inositol Phospholipid Kinase and Phosphoinositide-Specific Phospholipase C
349:
structure. Théodore
Posternak's work further elucidated the configuration of myo-inositol, the principal form found in eukaryotic tissues. The study of inositol
459:
on the three, four and five hydroxyl groups in seven different combinations. However, the two and six hydroxyl groups are typically not phosphorylated due to
1444:
Tabaei, Seyed R.; Guo, Feng; Rutaganira, Florentine U.; Vafaei, Setareh; Choong, Ingrid; Shokat, Kevan M.; Glenn, Jeffrey S.; Cho, Nam-Joon (2016-05-17).
611:
565:
1286:"Phosphatidylinositol-glycan-specific phospholipase D is an amphiphilic glycoprotein that in serum is associated with high-density lipoproteins"
1791:
Chatterjee, Soumya Deep; Zhou, Juan; Dasgupta, Rubin; Cramer-Blok, Anneloes; Timmer, Monika; van der Stelt, Mario; Ubbink, Marcellus (2021).
1762:
678:(ER), which is the largest membrane component of the cell. This site also contributes the synthesis to the majority of phospholipids, namely
604:
540:
524:
508:
391:
The discovery of PI and its derivatives, along with their intricate roles in cellular signaling, marks a significant chapter in the field of
746:, CDS- enzymes. In the final enzymatic process, CDP-DG and inositol are catalyzed by the enzyme PI synthase (PIS) and synthesised into PI.
72:
337:
Phosphatidylinositol (PI) and its derivatives have a rich history dating back to their discovery by Johann Joseph von
Scherer and
600:
493:
483:
473:
1229:"The "Other" Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances in myo -Inositol Chemistry)"
1940:
723:
acyl chain position. The process is then followed by a second acylation with LPAAT1, LPAAT2 and LPAAT3, LPAAT enzymes, at the
415:
PI can exist in nine different forms, myo-, scyllo-, muco-, epi-, neo-, allo-, D-chiro-, L-chiro-, and cis-inositol. These
1397:"SYMPOSIUM REVIEW: Phosphoinositides: lipid regulators of membrane proteins: Phosphoinositides instruct membrane proteins"
1333:"SYMPOSIUM REVIEW: Phosphoinositides: lipid regulators of membrane proteins: Phosphoinositides instruct membrane proteins"
977:"SYMPOSIUM REVIEW: Phosphoinositides: lipid regulators of membrane proteins: Phosphoinositides instruct membrane proteins"
252:
92:
1446:"Multistep Compositional Remodeling of Supported Lipid Membranes by Interfacially Active Phosphatidylinositol Kinases"
656:
345:" based on its sweet taste, the isolation and characterization of inositol laid the groundwork for understanding its
716:
1960:
1934:
1889:"Phosphatidylinositol 4,5-bisphosphate and calcium at ER-PM junctions — Complex interplay of simple messengers"
1600:"Phosphatidylinositol 4,5-bisphosphate and calcium at ER-PM junctions — Complex interplay of simple messengers"
683:
1285:
1395:
Falkenburger, Björn H.; Jensen, Jill B.; Dickson, Eamonn J.; Suh, Byung-Chang; Hille, Bertil (2010-09-01).
1331:
Falkenburger, Björn H.; Jensen, Jill B.; Dickson, Eamonn J.; Suh, Byung-Chang; Hille, Bertil (2010-09-01).
439:
Phosphorylated forms of phosphatidylinositol (PI) are called phosphoinositides and play important roles in
1955:
1640:
623:
1059:
Ballou, Clinton E.; Pizer, Lewis I. (1959). "SYNTHESIS OF AN OPTICALLY ACTIVE myo-INOSITOL 1-PHOSPHATE".
1024:
Pizer, Frances Lane; Ballou, Clinton E. (1959). "Studies on myo-Inositol
Phosphates of Natural Origin".
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638:
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280:
110:
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are common in biology and have many functions, for example taste sensory, regulating phosphate levels,
307:
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Falkenburger, Björn H.; Jensen, Jill B.; Dickson, Eamonn J.; Suh, Byung-Chang; Hille, Bertil (2010).
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cell membranes. The phosphate group imparts a negative charge to the molecules at physiological pH.
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738:(CDP-DG) by a process called CDP-diaglycerol synthase. This synthesis is catalyzed by the use of
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1793:"Protein Dynamics Influence the Enzymatic Activity of Phospholipase A/Acyltransferases 3 and 4"
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1688:"Phosphoinositide Diversity, Distribution, and Effector Function: Stepping Out of the Box"
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and their physiological functions has revealed a complex interplay in various organisms.
937:
151:
114:
oxyphosphoryl]oxy-2-octadecanoyloxypropyl] (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
1825:
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1182:"Ionization Properties of Phosphatidylinositol Polyphosphates in Mixed Model Membranes"
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1130:
1001:
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809:
Scherer, Johann J. (1850). "Uber eine neue aus dem
Muskelfleisch gewonnene Zuckerart".
452:
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sugar molecule. Typically, the phosphate group has a negative charge (at physiological
223:
1949:
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Kooijman, Edgar E.; King, Katrice E.; Gangoda, Mahinda; Gericke, Arne (2009-10-13).
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All seven variations of the following phosphoinositides have been found in animals:
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These phosphoinositides are also found in plant cells, with the exception of PIP
319:
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1865:
836:
Maquenne, Léon (1887). "Préparation, proprietés et constitution se l'inosite".
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and Dan Brown. Their pioneering work established the structure of PI and its
216:
887,104 g/mol, neutral with fatty acid composition - 18:0, 20:4
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1553:"Phosphatidyldmositol hydrolysis: A multifunctional transducing mechanism"
1510:
Biochimica et
Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids
1317:
768:
Biochimica et
Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids
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311:
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1096:"732. Phospholipids. Part VII. The structure of a monophosphoinositide"
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698:
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350:
342:
1227:
Thomas, Mark P.; Mills, Stephen J.; Potter, Barry V. L. (2016-01-26).
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702:
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The biosynthesis and phosphorylation of PI is mainly confined to the
416:
361:
222:
Except where otherwise noted, data are given for materials in their
876:
Comptes rendus hebdomadaires des séances de l'Académie des
Sciences
857:
Comptes rendus hebdomadaires des séances de l'Académie des Sciences
838:
Comptes rendus hebdomadaires des séances de l'Académie des Sciences
1686:
Choy, Christopher H.; Han, Bong-Kwan; Botelho, Roberto J. (2017).
655:
622:) and forms the second messengers, inositol (1,4,5) triphosphate (
596:
299:
142:
743:
727:
acyl chain position. This double step process acylates G-3-P to
694:(TG). The synthesis involves a series of enzymatic reactions.
275:. It was initially called "inosite" when it was discovered by
29:
1893:
Biochimica et Biophysica Acta (BBA) - Molecular Cell Research
1604:
Biochimica et Biophysica Acta (BBA) - Molecular Cell Research
1506:"Phosphatidylinositol synthesis at the endoplasmic reticulum"
764:"Phosphatidylinositol synthesis at the endoplasmic reticulum"
1850:"PLC regulation: emerging pictures for molecular mechanisms"
874:
Maquenne, Léon (1887). "Sur quelques dérivés de l'inosite".
315:
855:
Maquenne, Léon (1887). "Sur les propriétés de l'inosite".
641:). PA is also directly produced from phosphatidylcholine (
298:
The biomolecule can exist in 9 different isomers. It is a
1639:
Schink, Kay O.; Tan, Kia-Wee; Stenmark, Harald (2016).
240:
50:
603:), which is then converted into PI (4,5) biphosphate (
701:
facing surface of organelles by already residential
1641:"Phosphoinositides in Control of Membrane Dynamics"
1094:Brown, D. M.; Clark, B. F. C.; Letters, R. (1961).
633:). DG is then phosphyrylated to phosphatidic acid (
45:
may be too technical for most readers to understand
1747:Biochemistry of Lipids, Lipoproteins and Membranes
1504:Blunsom, Nicholas J.; Cockcroft, Shamshad (2020).
762:Blunsom, Nicholas J.; Cockcroft, Shamshad (2020).
922:"Acetonierung und Konfiguration des Meso-inosits"
325:The production of the molecule is limited to the
1645:Annual Review of Cell and Developmental Biology
674:of Phosphatidylinositol (PI) is limited to the
283:in the late 19th century. It was discovered in
1887:Ivanova, Adelina; Atakpa-Adaji, Peace (2023).
1598:Ivanova, Adelina; Atakpa-Adaji, Peace (2023).
341:in the late 19th century. Initially known as "
8:
1743:"Phospholipid Synthesis in Mammalian Cells"
84:
1933:at the U.S. National Library of Medicine
1904:
1824:
1615:
1477:
1420:
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1284:Hoener, Marius C.; Brodbeck, Urs (1992).
1260:
1156:
1146:
1100:Journal of the Chemical Society (Resumed)
1000:
610:) by the enzyme PI 4-phosphate-5-kinase (
364:, particularly PI, was first observed in
73:Learn how and when to remove this message
57:, without removing the technical details.
1061:Journal of the American Chemical Society
1026:Journal of the American Chemical Society
566:Phosphatidylinositol 3,4,5-trisphosphate
380:forms, shedding light on their roles as
1848:Bunney, Tom D.; Katan, Matilda (2011).
1233:Angewandte Chemie International Edition
754:
618:is then hydrolysed by phospholipase C (
170:
734:PA is converted into the intermediate
318:values). As a result, the molecule is
1941:Phosphatidylinositol at Lipid Library
1657:10.1146/annurev-cellbio-111315-125349
1499:
1497:
599:) converting PI into PI 4-phosphate (
541:Phosphatidylinositol 4,5-bisphosphate
525:Phosphatidylinositol 3,5-bisphosphate
509:Phosphatidylinositol 3,4-bisphosphate
469:Phosphatidylinositol monophosphates:
150:
55:make it understandable to non-experts
7:
1557:Molecular and Cellular Endocrinology
1131:"A short history of inositol lipids"
561:Phosphatidylinositol trisphosphate:
504:Phosphatidylinositol bisphosphates:
1755:10.1016/b978-0-444-63438-2.00007-9
1302:10.1111/j.1432-1033.1992.tb16981.x
711:PI synthesis of PI starts with an
705:, but not at the ER spesifically.
554:or often simply referred to as PIP
25:
1380:Muller-Roeber B, Pical C (2002).
1290:European Journal of Biochemistry
494:Phosphatidylinositol 5-phosphate
484:Phosphatidylinositol 4-phosphate
474:Phosphatidylinositol 3-phosphate
230:
91:
34:
719:(G-3-P) by GPAT enzymes at the
226:(at 25 °C , 100 kPa).
1854:Trends in Biochemical Sciences
1749:, Elsevier, pp. 209–236,
372:organisms by researchers like
333:History of phospatidylinositol
1:
1551:Berridge, Michael J. (1981).
568:, also known as PtdIns(3,4,5)
18:Inositol lipids and phosphate
1906:10.1016/j.bbamcr.2023.119475
1617:10.1016/j.bbamcr.2023.119475
1569:10.1016/0303-7207(81)90055-1
1522:10.1016/j.bbalip.2019.05.015
1462:10.1021/acs.analchem.6b01293
1413:10.1113/jphysiol.2010.192153
1349:10.1113/jphysiol.2010.192153
993:10.1113/jphysiol.2010.192153
780:10.1016/j.bbalip.2019.05.015
1809:10.1021/acs.biochem.0c00974
653:incapable of PI synthesis.
543:, also known as PtdIns(4,5)
527:, also known as PtdIns(3,5)
511:, also known as PtdIns(3,4)
451:. The inositol ring can be
356:The esterified presence of
1977:
1866:10.1016/j.tibs.2010.08.003
1741:Ridgway, Neale D. (2016),
717:Glyceraldehyde-3-phosphate
661:Blunsom and S. Cockcroft.
1401:The Journal of Physiology
1337:The Journal of Physiology
1135:Journal of Lipid Research
1129:Irvine, Robin F. (2016).
981:The Journal of Physiology
920:Dangschat, Gerda (1942).
281:Johann Joseph von Scherer
220:
181:
136:
119:
109:
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90:
1935:Medical Subject Headings
907:10.1002/hlca.19420250410
823:10.1002/jlac.18500730303
684:phosphatidylethanolamine
291:, and was found to be a
287:but later also found in
926:Die Naturwissenschaften
676:Endoplasmatic Reticulum
496:, also known as PtdIns5
486:, also known as PtdIns4
476:, also known as PtdIns3
403:Structure and chemistry
368:and later confirmed in
1704:10.1002/bies.201700121
1245:10.1002/anie.201502227
662:
645:) by phospholipase D (
629:) and diacylglycerol (
1931:Phosphatidylinositols
659:
327:endoplasmic reticulum
269:inositol phospholipid
86:Phosphatidylinositol
1450:Analytical Chemistry
1108:10.1039/jr9610003774
449:membrane trafficking
265:Phosphatidylinositol
1148:10.1194/jlr.R071712
1073:10.1021/ja01526a074
1038:10.1021/ja01513a040
938:1942NW.....30..146D
736:CDP- diacylglycerol
680:phosphatidylcholine
382:signaling molecules
87:
946:10.1007/BF01475387
688:phosphatidylserine
663:
397:cellular processes
386:signaling pathways
293:signaling molecule
253:Infobox references
85:
27:Signaling molecule
1803:(15): 1178–1190.
1764:978-0-444-63438-2
1456:(10): 5042–5045.
1407:(17): 3179–3185.
1343:(17): 3179–3185.
1198:10.1021/bi9008616
1192:(40): 9360–9371.
1141:(11): 1987–1994.
987:(17): 3179–3185.
932:(9–10): 146–147.
811:Liebigs Ann. Chem
729:phosphatidic acid
435:Phosphoinositides
308:fatty acid chains
302:which contains a
261:Chemical compound
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1822:
1818:
1814:
1810:
1806:
1802:
1798:
1794:
1787:
1784:
1774:
1770:
1766:
1760:
1756:
1752:
1748:
1744:
1737:
1734:
1729:
1725:
1721:
1717:
1713:
1709:
1705:
1701:
1697:
1693:
1689:
1682:
1679:
1674:
1670:
1666:
1662:
1658:
1654:
1650:
1646:
1642:
1635:
1632:
1627:
1623:
1618:
1613:
1610:(6): 119475.
1609:
1605:
1601:
1594:
1591:
1586:
1582:
1578:
1574:
1570:
1566:
1562:
1558:
1554:
1547:
1544:
1539:
1535:
1531:
1527:
1523:
1519:
1516:(1): 158471.
1515:
1511:
1507:
1500:
1498:
1494:
1489:
1485:
1480:
1475:
1471:
1467:
1463:
1459:
1455:
1451:
1447:
1440:
1437:
1432:
1428:
1423:
1418:
1414:
1410:
1406:
1402:
1398:
1391:
1388:
1383:
1376:
1373:
1368:
1364:
1359:
1354:
1350:
1346:
1342:
1338:
1334:
1327:
1324:
1319:
1315:
1311:
1307:
1303:
1299:
1295:
1291:
1287:
1280:
1277:
1272:
1268:
1263:
1258:
1254:
1250:
1246:
1242:
1238:
1234:
1230:
1223:
1220:
1215:
1211:
1207:
1203:
1199:
1195:
1191:
1187:
1183:
1176:
1173:
1168:
1164:
1159:
1154:
1149:
1144:
1140:
1136:
1132:
1125:
1122:
1117:
1113:
1109:
1105:
1102:: 3774–3779.
1101:
1097:
1090:
1087:
1082:
1078:
1074:
1070:
1066:
1062:
1055:
1052:
1047:
1043:
1039:
1035:
1031:
1027:
1020:
1017:
1012:
1008:
1003:
998:
994:
990:
986:
982:
978:
971:
968:
963:
959:
955:
951:
947:
943:
939:
935:
931:
928:(in German).
927:
923:
916:
913:
908:
904:
900:
896:
889:
886:
881:
877:
870:
867:
862:
858:
851:
848:
843:
839:
832:
829:
824:
820:
816:
812:
805:
802:
797:
793:
789:
785:
781:
777:
773:
769:
765:
758:
755:
749:
747:
745:
741:
737:
732:
730:
726:
722:
718:
714:
710:
709:
704:
700:
695:
693:
689:
685:
681:
677:
673:
665:
658:
654:
652:
648:
644:
640:
636:
632:
628:
621:
613:
609:
602:
598:
589:
587:
575:or PI(3,4,5)P
571:
567:
564:
563:
562:
546:
542:
539:
530:
526:
523:
514:
510:
507:
506:
505:
499:
495:
492:
489:
485:
482:
479:
475:
472:
471:
470:
467:
464:
462:
458:
454:
450:
446:
442:
434:
432:
429:
424:
422:
418:
413:
411:
402:
400:
398:
394:
389:
387:
383:
379:
375:
371:
367:
363:
359:
354:
352:
348:
344:
340:
339:LĂ©on Maquenne
332:
330:
328:
323:
321:
317:
313:
309:
305:
301:
296:
294:
290:
286:
282:
278:
277:LĂ©on Maquenne
274:
270:
266:
254:
247:
242:
225:
219:
215:
213:
210:
209:
193:
190:
186:
185:
180:
173:
169:
168:
166:
164:
161:
160:
153:
149:
148:
146:
144:
141:
140:
135:
127:
124:
123:
118:
112:
108:
103:
94:
89:
77:
74:
66:
63:February 2024
56:
52:
46:
43:This article
41:
32:
31:
19:
1896:
1892:
1882:
1860:(2): 88–96.
1857:
1853:
1843:
1800:
1797:Biochemistry
1796:
1786:
1776:, retrieved
1746:
1736:
1695:
1691:
1681:
1648:
1644:
1634:
1607:
1603:
1593:
1560:
1556:
1546:
1513:
1509:
1453:
1449:
1439:
1404:
1400:
1390:
1381:
1375:
1340:
1336:
1326:
1293:
1289:
1279:
1236:
1232:
1222:
1189:
1186:Biochemistry
1185:
1175:
1138:
1134:
1124:
1099:
1089:
1067:(17): 4745.
1064:
1060:
1054:
1029:
1025:
1019:
984:
980:
970:
929:
925:
915:
898:
894:
888:
882:: 1719-1722.
879:
875:
869:
860:
856:
850:
841:
837:
831:
814:
810:
804:
771:
767:
757:
733:
724:
720:
706:
696:
669:
666:Biosynthesis
651:mitochondria
593:
581:
569:
560:
544:
528:
512:
503:
497:
487:
477:
468:
465:
438:
425:
414:
406:
393:biochemistry
390:
355:
347:cyclohexanol
336:
324:
297:
268:
264:
263:
137:Identifiers
120:Other names
69:
60:
44:
715:process of
614:). PI(4,5)P
534:or PI(3,5)P
518:or PI(3,4)P
428:amphiphilic
320:amphiphilic
273:biomolecule
182:Properties
152:CHEBI:28874
1950:Categories
1778:2024-02-15
863:: 297-299.
844:: 225-227.
817:(3): 322.
750:References
590:Hydrolysis
550:, PI(4,5)P
410:eukaryotic
370:eukaryotic
310:, and one
289:eukaryotes
212:Molar mass
111:IUPAC name
99:Cockcroft.
1817:0006-2960
1712:0265-9247
1692:BioEssays
1665:1081-0706
1538:182948709
1470:0003-2700
1310:0014-2956
1253:1433-7851
1206:0006-2960
1116:0368-1769
1081:0002-7863
1046:0002-7863
954:0028-1042
796:182948709
699:cytosolic
690:(PS) and
672:synthesis
500:or PI(5)P
490:or PI(4)P
480:or PI(3)P
1915:37098393
1874:20870410
1835:33749246
1773:89265741
1728:22778474
1720:28977683
1673:27576122
1626:37098393
1585:27566538
1530:31173893
1488:27118725
1431:20519312
1367:20519312
1271:26694856
1214:19725516
1167:27623846
1011:20519312
962:38695213
788:31173893
713:acylated
605:PI(4,5)P
366:bacteria
358:inositol
312:inositol
285:bacteria
206:P
163:DrugBank
1826:8154263
1577:6117490
1479:5291064
1422:2976013
1358:2976013
1318:1606959
1262:5156312
1158:5087877
1002:2976013
934:Bibcode
731:(PA).
708:De novo
703:kinases
457:kinases
417:isomers
351:isomers
343:inosite
246:what is
244: (
172:DB02144
49:Please
1937:(MeSH)
1913:
1872:
1833:
1823:
1815:
1771:
1761:
1726:
1718:
1710:
1698:(12).
1671:
1663:
1624:
1583:
1575:
1536:
1528:
1486:
1476:
1468:
1429:
1419:
1365:
1355:
1316:
1308:
1269:
1259:
1251:
1212:
1204:
1165:
1155:
1114:
1079:
1044:
1009:
999:
960:
952:
794:
786:
686:(PE),
682:(PC),
612:PI4P5K
362:lipids
306:, two
241:verify
238:
128:PtdIns
105:Names
1769:S2CID
1724:S2CID
1581:S2CID
1534:S2CID
958:S2CID
792:S2CID
774:(1).
597:PI4Kα
300:lipid
271:is a
143:ChEBI
1911:PMID
1897:1870
1870:PMID
1831:PMID
1813:ISSN
1759:ISBN
1716:PMID
1708:ISSN
1669:PMID
1661:ISSN
1622:PMID
1608:1870
1573:PMID
1526:PMID
1514:1865
1484:PMID
1466:ISSN
1427:PMID
1363:PMID
1314:PMID
1306:ISSN
1267:PMID
1249:ISSN
1210:PMID
1202:ISSN
1163:PMID
1112:ISSN
1077:ISSN
1042:ISSN
1007:PMID
950:ISSN
784:PMID
772:1865
744:CDS2
742:and
740:CDS1
725:sn-2
721:sn-1
670:The
601:PI4P
447:and
279:and
1901:doi
1862:doi
1821:PMC
1805:doi
1751:doi
1700:doi
1653:doi
1612:doi
1565:doi
1518:doi
1474:PMC
1458:doi
1417:PMC
1409:doi
1405:588
1353:PMC
1345:doi
1341:588
1298:doi
1294:206
1257:PMC
1241:doi
1194:doi
1153:PMC
1143:doi
1104:doi
1069:doi
1034:doi
997:PMC
989:doi
985:588
942:doi
903:doi
880:104
861:104
842:104
819:doi
776:doi
647:PLD
639:DGK
620:PLC
399:.
360:in
267:or
53:to
1952::
1909:.
1895:.
1891:.
1868:.
1858:36
1856:.
1852:.
1829:.
1819:.
1811:.
1801:60
1799:.
1795:.
1767:,
1757:,
1745:,
1722:.
1714:.
1706:.
1696:39
1694:.
1690:.
1667:.
1659:.
1649:32
1647:.
1643:.
1620:.
1606:.
1602:.
1579:.
1571:.
1561:24
1559:.
1555:.
1532:.
1524:.
1512:.
1508:.
1496:^
1482:.
1472:.
1464:.
1454:88
1452:.
1448:.
1425:.
1415:.
1403:.
1399:.
1361:.
1351:.
1339:.
1335:.
1312:.
1304:.
1292:.
1288:.
1265:.
1255:.
1247:.
1237:55
1235:.
1231:.
1208:.
1200:.
1190:48
1188:.
1184:.
1161:.
1151:.
1139:57
1137:.
1133:.
1110:.
1098:.
1075:.
1065:81
1063:.
1040:.
1030:81
1028:.
1005:.
995:.
983:.
979:.
956:.
948:.
940:.
930:30
924:.
899:25
897:.
878:.
859:.
840:.
815:73
813:.
790:.
782:.
770:.
766:.
643:PC
635:PA
631:DG
624:IP
586:.
463:.
443:,
388:.
329:.
322:.
316:pH
295:.
204:13
200:83
196:47
125:PI
1917:.
1903::
1876:.
1864::
1837:.
1807::
1753::
1730:.
1702::
1675:.
1655::
1628:.
1614::
1587:.
1567::
1540:.
1520::
1490:.
1460::
1433:.
1411::
1384:.
1369:.
1347::
1320:.
1300::
1273:.
1243::
1216:.
1196::
1169:.
1145::
1118:.
1106::
1083:.
1071::
1048:.
1036::
1013:.
991::
964:.
944::
936::
909:.
905::
825:.
821::
798:.
778::
626:3
616:2
607:2
595:(
584:3
577:3
573:3
570:P
556:2
552:2
548:2
545:P
536:2
532:2
529:P
520:2
516:2
513:P
498:P
488:P
478:P
236:Y
202:O
198:H
194:C
76:)
70:(
65:)
61:(
47:.
20:)
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