Record Information
Version2.0
Creation Date2012-05-31 14:04:37 -0600
Update Date2015-09-13 12:56:13 -0600
Secondary Accession Numbers
  • ECMDB04087
Identification
Name:Myoinositol
DescriptionInositol is a cyclic polyalcohol. It exists in nine possible stereoisomers, of which the most prominent form, widely occurring in nature, is cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol. It is an isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin. Foods containing the highest concentrations of myo-inositol include fruits, beans, grains and nuts.
Structure
Thumb
Synonyms:
  • meso-inositol
  • Chiro-inositol
  • Cis-1,2,3,5-trans-4,6-Cyclohexanehexol
  • Dambose
  • I-Inositol
  • Inositol
  • Iso-Inositol
  • M-Inositol
  • Meat sugar
  • Meso-Inositol
  • Mesoinositol
  • MI
  • Myo-Inositol
  • Myoinosite
  • Myoinositol
  • Phaseomannite
  • Rat antispectacled eye factor
Chemical Formula:C6H12O6
Weight:Average: 180.1559
Monoisotopic: 180.063388116
InChI Key:CDAISMWEOUEBRE-GPIVLXJGSA-N
InChI:InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-
CAS number:87-89-8
IUPAC Name:(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional IUPAC Name:L-inositol
SMILES:O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Sugar alcohol
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Polyol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:225 °C
Experimental Properties:
PropertyValueSource
Water Solubility:143 mg/mL at 19 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 143.0 mg/mL at 19 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility485 g/LALOGPS
logP-2.6ALOGPS
logP-3.8ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.77 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-014j-0953000000-1571a0577293e96091b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-00kb-0932000000-96ddc21293431d746ad2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0942000000-b78076224adf13bade25View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0942000000-42c4e40d04b4f306535dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-00di-8942000000-f5d7abd38d6ff547a0a9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-066r-0975000000-df7304c12b6c9bdb0f76View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-0953000000-1571a0577293e96091b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0932000000-96ddc21293431d746ad2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0942000000-b78076224adf13bade25View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8942000000-f5d7abd38d6ff547a0a9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066r-0975000000-df7304c12b6c9bdb0f76View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-9700000000-18a13ab4150e6ebb20cdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-00fr-9001040000-00e67b437c4329aee95dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a59-3900000000-96084971c3e13a1e7451View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-1de17d7f53ca727e6d72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0zh9-9000000000-bef910214341056a78aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-41a49af846b1636763b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-06f9ecfccf30d40ef204View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-004i-0900000000-bca88f6782a8ed386223View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-004i-1900000000-500ab195d69568b8678bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-01ti-5900000000-a1657b54c985e2be1d19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-000i-9600000000-325cbb8dbfdeafb2b31fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-9200000000-9145a4766351204e723aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-000i-9100000000-2bbbcfa4733b749ec768View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-000i-9000000000-de0ec8731a152b612bb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-0079-9000000000-41d049d1feef94e190d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-059i-9000000000-796e728daf28d5122deeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-059i-9000000000-8643e206319f3008a8d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0abi-9000000000-98e61f19bc2842f2e97bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0ab9-9000000000-29aa062fc4d5341167b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-03di-1900000000-5a2897fd032a959918b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000i-9000000000-71c4786b7034d5a0a0a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5cb39f92646251665ebfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2aeb7708f31c772e2d95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8900000000-74f89711a1c6891808a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8b68ff47f846a8ca1dddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-03ef8572289795275d9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-9300000000-950a37bd331028801e9fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Ashwal S, Holshouser B, Tong K, Serna T, Osterdock R, Gross M, Kido D: Proton spectroscopy detected myoinositol in children with traumatic brain injury. Pediatr Res. 2004 Oct;56(4):630-8. Epub 2004 Aug 4. Pubmed: 15295080
  • Chang L, Ernst T, Leonido-Yee M, Witt M, Speck O, Walot I, Miller EN: Highly active antiretroviral therapy reverses brain metabolite abnormalities in mild HIV dementia. Neurology. 1999 Sep 11;53(4):782-9. Pubmed: 10489041
  • Chang L, Lee PL, Yiannoutsos CT, Ernst T, Marra CM, Richards T, Kolson D, Schifitto G, Jarvik JG, Miller EN, Lenkinski R, Gonzalez G, Navia BA: A multicenter in vivo proton-MRS study of HIV-associated dementia and its relationship to age. Neuroimage. 2004 Dec;23(4):1336-47. Pubmed: 15589098
  • Cordoba J, Hinojosa C, Sampedro F, Alonso J, Rovira A, Quiroga S, Esteban R, Guardia J: Usefulness of magnetic resonance spectroscopy for diagnosis of hepatic encephalopathy in a patient with relapsing confusional syndrome. Dig Dis Sci. 2001 Nov;46(11):2451-5. Pubmed: 11713951
  • Ernst T, Itti E, Itti L, Chang L: Changes in cerebral metabolism are detected prior to perfusion changes in early HIV-CMC: A coregistered (1)H MRS and SPECT study. J Magn Reson Imaging. 2000 Dec;12(6):859-65. Pubmed: 11105023
  • Galasko GT, Bao Y, Broomfield SJ, Hooper NM, Turner AJ, Larner J: Circulating factors and insulin resistance. I. A novel myoinositol 1,2-cyclic phosphate phosphoglycan insulin antagonist from human plasma is elevated in noninsulin-dependent diabetes mellitus. J Clin Endocrinol Metab. 1995 Aug;80(8):2419-29. Pubmed: 7629237
  • Gryz EA, Galicka-Latala D, Szczudlik A, Sieradzki J: [Etiopathogenesis of diabetic neuropathy] Przegl Lek. 2000;57(12):727-31. Pubmed: 11398597
  • Grzelec H: [Pathogenesis and treatment of diabetic neuropathy] Neurol Neurochir Pol. 1991 Jul-Aug;25(4):477-84. Pubmed: 1666426
  • Hallman M, Saugstad OD, Porreco RP, Epstein BL, Gluck L: Role of myoinositol in regulation of surfactant phospholipids in the newborn. Early Hum Dev. 1985 Jan;10(3-4):245-54. Pubmed: 3838720
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kim MO, Im JH, Choi CG, Lee MC: Proton MR spectroscopic findings in paroxysmal kinesigenic dyskinesia. Mov Disord. 1998 May;13(3):570-5. Pubmed: 9613757
  • Kusmierz J, DeGeorge JJ, Sweeney D, May C, Rapoport SI: Quantitative analysis of polyols in human plasma and cerebrospinal fluid. J Chromatogr. 1989 Dec 29;497:39-48. Pubmed: 2625478
  • Lee PL, Yiannoutsos CT, Ernst T, Chang L, Marra CM, Jarvik JG, Richards TL, Kwok EW, Kolson DL, Simpson D, Tang CY, Schifitto G, Ketonen LM, Meyerhoff DJ, Lenkinski RE, Gonzalez RG, Navia BA: A multi-center 1H MRS study of the AIDS dementia complex: validation and preliminary analysis. J Magn Reson Imaging. 2003 Jun;17(6):625-33. Pubmed: 12766890
  • Reznek RH, Salway JG, Thomas PK: Plasma-myoinositol concentrations in uraemic neuropathy. Lancet. 1977 Mar 26;1(8013):675-6. Pubmed: 66475
  • Rysz J, Bartnicki P, Blaszczak R, Kujawski K, Cialkowska-Rysz A, Olszewski R, Markuszewski L: [Anti-inflammatory action of myoinositol in renal insufficiency] Pol Merkur Lekarski. 2006 Feb;20(116):180-3. Pubmed: 16708635
  • Scully SE, Stebner FC, Yoest SM: Magnetic resonance spectroscopic findings in neuro-Behcet disease. Neurologist. 2004 Nov;10(6):323-6. Pubmed: 15518598
  • Servo C, Pitkanen E: Variation in polyol levels in cerebrospinal fluid and serum in diabetic patients. Diabetologia. 1975 Dec;11(6):575-80. Pubmed: 1205026
  • Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. Pubmed: 7710082
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Utriainen M, Komu M, Vuorinen V, Lehikoinen P, Sonninen P, Kurki T, Utriainen T, Roivainen A, Kalimo H, Minn H: Evaluation of brain tumor metabolism with [11C]choline PET and 1H-MRS. J Neurooncol. 2003 May;62(3):329-38. Pubmed: 12777086
  • Wuarin-Bierman L, Zahnd GR: Current aspects of research on the pathogenesis of diabetic neuropathy. Diabete Metab. 1986 Dec;12(6):319-24. Pubmed: 3028879
  • Yiannoutsos CT, Ernst T, Chang L, Lee PL, Richards T, Marra CM, Meyerhoff DJ, Jarvik JG, Kolson D, Schifitto G, Ellis RJ, Swindells S, Simpson DM, Miller EN, Gonzalez RG, Navia BA: Regional patterns of brain metabolites in AIDS dementia complex. Neuroimage. 2004 Nov;23(3):928-35. Pubmed: 15528093
Synthesis Reference:Iselin, Beat M. Synthesis of inositol-5-monophosphoric acid and scyllitol monophosphoric acid. Journal of the American Chemical Society (1949), 71 3822-5.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17268
HMDB IDHMDB00211
Pubchem Compound ID892
Kegg IDC00137
ChemSpider ID10239179
WikipediaMI
BioCyc IDMYO-INOSITOL
EcoCyc IDMYO-INOSITOL
Ligand ExpoINS

Enzymes

General function:
Involved in phosphatidylinositol phosphorylation
Specific function:
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate
Gene Name:
suhB
Uniprot ID:
P0ADG4
Molecular weight:
29172
Reactions
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate.