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Record Information
Version3.6
Creation Date2006-08-12 22:06:07 UTC
Update Date2016-02-11 01:06:20 UTC
HMDB IDHMDB03502
Secondary Accession NumbersNone
Metabolite Identification
Common NameMyo-inositol hexakisphosphate
DescriptionMyo-Inositol hexakisphosphate is an intermediate in inositol phosphate metabolism. It can be generated from D-myo-Inositol 1,3,4,5,6-pentakisphosphate via the enzyme inositol-pentakisphosphate 2-kinase (EC:2.7.1.158). Myo-Inositol hexakisphosphate is also known as phytic acid. It can be used clinically as a complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent. Phytic acid is a strong chelator of important minerals such as calcium, magnesium, iron and zinc and can therefore contribute to mineral deficiencies in developing countries. For people with a particularly low intake of essential minerals, especially young children and those in developing countries, this effect can be undesirable. However, dietary mineral chelators help prevent over-mineralization of joints, blood vessels, and other parts of the body, which is most common in older persons. The Journal of Environmental Nutrition (April 2004 volume 27 issue 4) has also stated phytic acid may be considered a phytonutrient, providing an antioxidant effect.
Structure
Thumb
Synonyms
ValueSource
1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphateHMDB
1D-myo-Inositol hexakisphosphateHMDB
D-myo-Inositol 1,2,3,4,5,6-hexakisphosphateHMDB
Inositol 1,2,3,4,5,6-hexakisphosphateHMDB
myo-Inositol 1,2,3,4,5,6-hexakisphosphateHMDB
PhytateHMDB
Phytic acidHMDB
Chemical FormulaC6H18O24P6
Average Molecular Weight660.0353
Monoisotopic Molecular Weight659.861370576
IUPAC Name{[2,3,4,5,6-pentakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Namephytic acid
CAS Registry Number83-86-3
SMILES
OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O
InChI Identifier
InChI=1S/C6H18O24P6/c7-31(8,9)25-1-2(26-32(10,11)12)4(28-34(16,17)18)6(30-36(22,23)24)5(29-35(19,20)21)3(1)27-33(13,14)15/h1-6H,(H2,7,8,9)(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)(H2,19,20,21)(H2,22,23,24)
InChI KeyInChIKey=IMQLKJBTEOYOSI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as inositol phosphates. These are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.7 mg/mLALOGPS
logP0.11ALOGPS
logP-4.5ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.14ChemAxon
Physiological Charge-12ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area400.56 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity101.01 m3·mol-1ChemAxon
Polarizability42.76 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2000029000-170b59b987d1793da521View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2000029000-2abfcb8b1f82e5ed9d0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5000910000-898702e2b03bf951e93bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4000009000-9f6af14cfd403477a602View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000002000-e40f60df66da33ed1adcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4637889507d0d883c7beView in MoNA
Biological Properties
Cellular Locations
  • Nucleus
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Liver
  • Pancreas
  • Prostate
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Inositol MetabolismSMP00011map00562
Inositol Phosphate MetabolismSMP00462map00562
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.34 (0.21-0.46) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.39 (0.65-3.82) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000374
KNApSAcK IDNot Available
Chemspider ID866
KEGG Compound IDC01204
BioCyc IDMI-HEXAKISPHOSPHATE
BiGG ID37070
Wikipedia LinkPhytate
NuGOwiki LinkHMDB03502
Metagene LinkHMDB03502
METLIN ID6941
PubChem Compound890
PDB IDNot Available
ChEBI ID17401
References
Synthesis ReferenceMitsuhashi Naoto; Ohnishi Miwa; Sekiguchi Yoko; Kwon Yong-Uk; Chang Young-Tae; Chung Sung-Kee; Inoue Yoshinori; Reid Robert J; Yagisawa Hitoshi; Mimura Tetsuro Phytic acid synthesis and vacuolar accumulation in suspension-cultured cells of Catharanthus roseus induced by high concentration of inorganic phosphate and cations. Plant physiology (2005), 138(3), 1607-14.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hirano T, Tomiyoshi K, Take H, Watanabe N, Oriuchi N, Inoue T, Naruse M, Endo K: Reversible functional asplenia. Autoimmune hemolytic anemia with thrombocytopenia in chronic lymphocytic leukemia. Clin Nucl Med. 1994 Aug;19(8):693-5. [7955748 ]
  2. Ikeda K, Tsuji H, Nomiyama K, Ishitsuka T, Murai K, Akagi K, Fujishima M, Ichiya Y, Shiraishi A, Tsubota Y: [A case of alcoholic cirrhosis demonstrating long-term poor-visualization of the hepatic image on 99mTc-phytate scintigraphy] Fukuoka Igaku Zasshi. 1990 Apr;81(4):186-91. [2379909 ]
  3. Fox CH, Eberl M: Phytic acid (IP6), novel broad spectrum anti-neoplastic agent: a systematic review. Complement Ther Med. 2002 Dec;10(4):229-34. [12594974 ]
  4. Balashov AT, Mendeleev IM: [Roentgenoradiological and ultrasonic diagnosis of liver and spleen involvement in patients with Hodgkin's disease] Ter Arkh. 1988;60(9):73-6. [3064339 ]
  5. Dilworth LL, Omoruyi FO, Simon OR, Morrison EY, Asemota HN: The effect of phytic acid on the levels of blood glucose and some enzymes of carbohydrate and lipid metabolism. West Indian Med J. 2005 Mar;54(2):102-6. [15999878 ]
  6. Shiomi S, Kuroki T, Ueda T, Ikeoka N, Kobayashi K, Ochi H: Hypereosinophilic syndrome appearing as a focal defect on liver scan. Ann Nucl Med. 1991 Nov;5(4):171-3. [1797073 ]
  7. Groshar D, Slobodin G, Zuckerman E: Quantitation of liver and spleen uptake of (99m)Tc-phytate colloid using SPECT: detection of liver cirrhosis. J Nucl Med. 2002 Mar;43(3):312-7. [11884489 ]
  8. Takashima H, Egawa M, Imao T, Fukuda M, Yokoyama K, Namiki M: Validity of sentinel lymph node concept for patients with prostate cancer. J Urol. 2004 Jun;171(6 Pt 1):2268-71. [15126800 ]
  9. Shiomi S, Kuroki T, Kitada T, Nakajima S, Kobayashi K, Ochi H: Finding of right hepatic vein focal defect in liver scan of a patient with veno-occlusive disease. Clin Nucl Med. 1993 Nov;18(11):958-60. [8269677 ]
  10. Kume N, Suga K, Nishigauchi K, Uchisako H, Sugano A, Fujita T, Nakanishi T, Hamasaki T, Suzuki T: [Evaluation of pancreatic cancers using thallium-201 single photon emission computed tomography] Nippon Igaku Hoshasen Gakkai Zasshi. 1995 Aug;55(9):682-9. [7478955 ]
  11. Morita S, Nishi F, Kajiwara Y, Dannoura R, Oshibuchi M, Kikuchi S, Ohtake H, Takeoka A: [A case report of horseshoe kidney incidentally detected by Tc-99m-phytate liver scintigraphy] Rinsho Hoshasen. 1984 Mar;29(3):427-9. [6748283 ]
  12. Nishiguchi S, Habu D, Ishizu H, Iwata Y, Tatsumi N, Enomoto M, Minamitani S, Fukuda K, Tamori A, Takeda T, Shiomi S, Kawabe J, Ochi H: Accessory spleen in the pelvis diagnosed by Tc-99m phytate scintigraphy. Ann Nucl Med. 2001 Jun;15(3):263-5. [11545199 ]
  13. Ohta H, Kohno K, Kojima N, Ihara N, Ishigaki T, Todo G, Komibuchi T: A case of diaphragm hernia containing accessory spleen and great omentum detected by Tc-99m phytate scintigraphy. Ann Nucl Med. 1999 Oct;13(5):347-9. [10582805 ]
  14. Irisawa A, Obara K, Bhutani MS, Saito A, Shishido H, Shibukawa G, Takagi T, Yamamoto G, Seino O, Shishido F, Kasukawa R, Sato Y: Role of para-esophageal collateral veins in patients with portal hypertension based on the results of endoscopic ultrasonography and liver scintigraphy analysis. J Gastroenterol Hepatol. 2003 Mar;18(3):309-14. [12603532 ]

Enzymes

General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Acts as a modulator of macrophage activation through control of glucose metabolism (By similarity).
Gene Name:
SHPK
Uniprot ID:
Q9UHJ6
Molecular weight:
51504.425
General function:
Involved in acid phosphatase activity
Specific function:
Acts as a phosphoinositide 5- and phosphoinositide 6-phosphatase and regulates cellular levels of inositol pentakisphosphate (InsP5) and inositol hexakisphosphate (InsP6). Also acts as a 2,3-bisphosphoglycerate 3-phosphatase, by mediating the dephosphorylation of 2,3-bisphosphoglycerate (2,3-BPG) to produce phospho-D-glycerate without formation of 3-phosphoglycerate. May play a role in bone development (endochondral ossification).
Gene Name:
MINPP1
Uniprot ID:
Q9UNW1
Molecular weight:
34660.555
Reactions
Myo-inositol hexakisphosphate + Water → myo-inositol pentakisphosphate (mixed isomers) + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate), suggesting that it may play a role in signal transduction. Also able to catalyze the hydrolysis of dinucleoside oligophosphates, with Ap6A and Ap5A being the preferred substrates. The major reaction products are ADP and p4a from Ap6A and ADP and ATP from Ap5A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT11
Uniprot ID:
Q96G61
Molecular weight:
18558.835
General function:
Involved in hydrolase activity
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate) and [PP]2-InsP4 (bisdiphosphoinositol tetrakisphosphate), suggesting that it may play a role in signal transduction. InsP6 (inositol hexakisphophate) is not a substrate. Acts as a negative regulator of the ERK1/2 pathway. Also able to catalyze the hydrolysis of dinucleoside oligophosphates, with Ap6A and Ap5A being the preferred substrates. The major reaction products are ADP and p4a from Ap6A and ADP and ATP from Ap5A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT3
Uniprot ID:
O95989
Molecular weight:
19470.855
General function:
Involved in hydrolase activity
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate), PP-InsP4 and [PP]2-InsP4 (bisdiphosphoinositol tetrakisphosphate), suggesting that it may play a role in signal transduction. Also able to catalyze the hydrolysis of dinucleoside oligophosphate Ap6A, but not Ap5A. The major reaction products are ADP and p4a from Ap6A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT4
Uniprot ID:
Q9NZJ9
Molecular weight:
20305.895
General function:
Involved in ATP binding
Specific function:
Phosphorylates Ins(1,3,4,5,6)P5 at position 2 to form Ins(1,2,3,4,5,6)P6 (InsP6 or phytate). InsP6 is involved in many processes such as mRNA export, non-homologous end-joining, endocytosis, ion channel regulation. It also protects cells from TNF-alpha-induced apoptosis.
Gene Name:
IPPK
Uniprot ID:
Q9H8X2
Molecular weight:
56016.12
Reactions
Myo-inositol hexakisphosphate + ADP → Inositol 1,3,4,5,6-pentakisphosphate + Adenosine triphosphatedetails
General function:
Involved in inositol trisphosphate 3-kinase activity
Specific function:
Not Available
Gene Name:
IHPK3
Uniprot ID:
Q5TAQ4
Molecular weight:
46416.3
General function:
Involved in inositol trisphosphate 3-kinase activity
Specific function:
Not Available
Gene Name:
IP6K1
Uniprot ID:
Q92551
Molecular weight:
31523.6