Inositol pentakisphosphate

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

Identifiers
CAS Number	20298-95-7 [1]
3D model (Jmol)	Interactive image
ChEBI	CHEBI:57733
ChemSpider	19951265
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+ Key: CTPQAXVNYGZUAJ-KXXVROSKSA-D 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
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
Properties
Chemical formula	C6H17O21P5
Molar mass	580.05 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

1. Sigma Aldrich
2. 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.
3. 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.
4. 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.