You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 22:06:07 UTC
Update Date2019-07-23 05:45:48 UTC
HMDB IDHMDB0003502
Secondary Accession Numbers
  • HMDB03502
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
Data?1563860748
Synonyms
ValueSource
1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphateChEBI
1D-myo-Inositol hexakisphosphateChEBI
Acide fytiqueChEBI
acido FiticoChEBI
Acidum fyticumChEBI
D-myo-Inositol 1,2,3,4,5,6-hexakisphosphateChEBI
InosithexaphosphorsaeureChEBI
myo-Inositol 1,2,3,4,5,6-hexakisphosphateChEBI
PhytateChEBI
PhytineChEBI
Saeure des phytinsChEBI
1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphoric acidGenerator
1D-myo-Inositol hexakisphosphoric acidGenerator
D-myo-Inositol 1,2,3,4,5,6-hexakisphosphoric acidGenerator
myo-Inositol 1,2,3,4,5,6-hexakisphosphoric acidGenerator
Inositol 1,2,3,4,5,6-hexakisphosphateHMDB
Inositol hexakis(phosphate)HMDB
Inositol hexaphosphateHMDB
Phytic acidHMDB
meso-Inositol hexaphosphateHMDB
myo-Inositol hexakis(phosphate)HMDB
myo-Inositol hexakisphosphateHMDB
myo-Inositol hexaphosphateHMDB
Chemical FormulaC6H18O24P6
Average Molecular Weight660.0353
Monoisotopic Molecular Weight659.861370576
IUPAC Name{[(1s,2R,3R,4r,5S,6S)-2,3,4,5,6-pentakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1s,2R,3R,4r,5S,6S)-2,3,4,5,6-pentakis(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry Number83-86-3
SMILES
OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(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)/t1-,2-,3-,4+,5-,6-
InChI KeyIMQLKJBTEOYOSI-GPIVLXJGSA-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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity101.01 m³·mol⁻¹ChemAxon
Polarizability42.6 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9010130000-79789c04eb088a4921f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2000029000-170b59b987d1793da521JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2000029000-2abfcb8b1f82e5ed9d0fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5000910000-898702e2b03bf951e93bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4000009000-9f6af14cfd403477a602JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000002000-e40f60df66da33ed1adcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4637889507d0d883c7beJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Nucleus
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Liver
  • Pancreas
  • Prostate
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000374
KNApSAcK IDNot Available
Chemspider ID16735966
KEGG Compound IDC01204
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhytic acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDI6P
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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]. Nihon Igaku Hoshasen Gakkai Zasshi. 1995 Aug;55(9):682-9. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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) + Phosphatedetails
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