Inositol pentakisphosphate

myo-Inositol 1,3,4,5,6-pentakisphosphate

Identifiers
CAS number	20298-95-7, ^[1]
ChemSpider	19951265^Y
ChEBI	CHEBI:57733^Y
Jmol-3D images	Image 1
SMILES O=P([O-])([O-])O[C@@H]1[C@@H](OP([O-])([O-])=O)[C@H](OP([O-])([O-])=O)[C@H](O)[C@H](OP([O-])([O-])=O)[C@H]1OP([O-])([O-])=O
InChI InChI=1S/C6H17O21P5/c7-1-2(23-28(8,9)10)4(25-30(14,15)16)6(27-32(20,21)22)5(26-31(17,18)19)3(1)24-29(11,12)13/h1-7H,(H2,8,9,10)(H2,11,12,13)(H2,14,15,16)(H2,17,18,19)(H2,20,21,22)/p-10/t1-,2+,3-,4-,5+,6+^Y Key: CTPQAXVNYGZUAJ-KXXVROSKSA-D^Y InChI=1/C6H17O21P5/c7-1-2(23-28(8,9)10)4(25-30(14,15)16)6(27-32(20,21)22)5(26-31(17,18)19)3(1)24-29(11,12)13/h1-7H,(H2,8,9,10)(H2,11,12,13)(H2,14,15,16)(H2,17,18,19)(H2,20,21,22)/p-10/t1-,2+,3-,4-,5+,6+ Key: CTPQAXVNYGZUAJ-JSZKNSOJBF
Properties
Molecular formula	C₆H₁₇O₂₁P₅
Molar mass	580.06 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Inositol pentakisphosphate (abbreviated IP5) is a molecule derived from inositol tetrakisphosphate by adding a phosphate group with the help of inositol polyphosphate multikinase (IPMK). It is believed to be one of the many second messengers in the inositol phosphate family. It "is implicated in a wide array of biological and pathophysiological responses, including tumorigenesis, invasion and metastasis, therefore specific inhibitors of the kinase may prove useful in cancer therapy."^[2]

IP5 also plays a role in defense signaling in plants. It potentiates the interaction of the plant hormone JA-Ile by its receptor.^[3]^[4]

References

^ Sigma Aldrich
^ Piccolo, E.; Vignati, S.; Maffucci, T.; Innominato, P. F.; Riley, A. M.; Potter, B. V.; Pandolfi, P. P.; Broggini, M. et al. (2004). "Inositol pentakisphosphate promotes apoptosis through the PI 3-K/Akt pathway". Oncogene 23 (9): 1754–1765. doi:10.1038/sj.onc.1207296. PMID 14755253.
^ Sheard, L. B.; Tan, Xu; Mao, Haibin; Withers, John; Ben-Nissan, Gili; Hinds, Thomas R.; Kobayashi, Yuichi; Hsu, Fong-Fu et al. (2010). "Jasmonate perception by inositol phosphate-potentiated COI1-JAZ co-receptor". Nature 468 (7322): 400–405. doi:10.1038/nature09430. PMC 2988090. PMID 20927106. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2988090.
^ Mosblech, A.; Thurow, Corinna; Gatz, Christiane; Feussner, Ivo; Heilmann, Ingo (2010). "Jasmonic acid perception by COI1 involves inositol polyphosphates in Arabidopsis thaliana". The Plant Journal 65 (6): 949–957. doi:10.1111/j.1365-313X.2011.04480.x. PMID 21205029.