Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:05 UTC
HMDB IDHMDB00211
Secondary Accession Numbers
  • HMDB02256
Metabolite Identification
Common NameMyoinositol
DescriptionInositol is a cyclic polyalcohol that plays an important role as a second messenger in a cell, in the form of inositol phosphates. It is found in many foods, particularly in cereals with high bran content. 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 and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed., p1379) Inositol phospholipids are important in signal transduction.
Structure
Thumb
Synonyms
  1. cis-1,2,3,5-trans-4,6-Cyclohexanehexol
  2. i-Inositol
  3. Iso-Inositol
  4. Meat sugar
  5. Meso-Inositol
  6. MI
  7. Myo-Inositol
  8. Myoinosite
  9. Myoinositol
  10. Phaseomannite
  11. Rat antispectacled eye factor
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional IUPAC Namemyo-inositol
CAS Registry Number87-89-8
SMILES
O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-
InChI KeyCDAISMWEOUEBRE-GPIVLXJGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Homomonocyclic Compounds
ClassCyclic Alcohols and Derivatives
Sub ClassCyclitols and Derivatives
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • chiro-inositol(ChEBI)
Substituents
  • 1,2 Diol
  • Cyclohexane
  • Saccharide
  • Secondary Alcohol
  • Sugar Alcohol
Direct ParentCyclitols and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerophospholipid metabolism
  • Component of Inositol phosphate metabolism
  • Component of Streptomycin biosynthesis
  • Osmolyte
  • Second messenger
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility143 mg/mL at 19 °CHuman Metabolome Project
LogPNot AvailableNot Available
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 area121.38ChemAxon
rotatable bond count0ChemAxon
refractivity35.77ChemAxon
polarizability16.14ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Basal Ganglia
  • Brain
  • Fibroblasts
  • Intestine
  • Kidney
  • Myelin
  • Nerve Cells
  • Neuron
  • Prostate
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
Inositol MetabolismSMP00011map00562
Inositol Phosphate MetabolismSMP00462map00562
Phosphatidylinositol Phosphate MetabolismSMP00463map00562
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified17.1 uMAdult (>18 years old)Not SpecifiedNormal
BloodDetected and Quantified24.0 +/- 7.8 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified23.0 +/- 8.0 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified 30.0 (21.0-49.0) uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified174.0 +/- 31.0 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified84 +/- 40 uMNot SpecifiedBothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified158.8 +/- 46.07 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified138.3 +/- 24.4 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified133.0 (111.0-155.0) uMAdult (>18 years old)BothNormal
UrineDetected and Quantified12.6 (5.1-15.3) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified18.8 +/- 2.9 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
UrineDetected and Quantified22.4 (7.9-36.1) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified52.8 +/- 47.7 umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
UrineDetected and Quantified6.11 +/- 6.25 umol/mmol creatinineInfant (0-1 year old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified20.0 (23.0–24.0) uMAdult (>18 years old)BothRibose-5-phosphate isomerase deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified158.8 +/- 27.2 uMAdult (>18 years old)BothAlzheimer's disease
Cerebrospinal Fluid (CSF)Detected and Quantified158.8 +/- 27.2 uMNot SpecifiedNot SpecifiedAlzheimer's disease
UrineDetected and Quantified20.33 +/- 13.70 umol/mmol creatinineAdult (>18 years old)Not SpecifiedCachexia
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. Pubmed: 8595727
Cachexia
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. Pubmed: 18953024
Ribose-5-phosphate isomerase deficiency
  • Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. Pubmed: 14988808
Associated OMIM IDs
    104300 (Alzheimer's disease)608611 (Ribose-5-phosphate isomerase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB010547
KNApSAcK IDC00001164
Chemspider ID10239179
KEGG Compound IDC00137
BioCyc IDMYO-INOSITOL
BiGG ID33990
Wikipedia LinkMI
NuGOwiki LinkHMDB00211
Metagene LinkHMDB00211
METLIN ID5221
PubChem CompoundNot Available
PDB IDINS
ChEBI ID17268
References
Synthesis ReferenceIselin, 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)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. Gryz EA, Galicka-Latala D, Szczudlik A, Sieradzki J: [Etiopathogenesis of diabetic neuropathy] Przegl Lek. 2000;57(12):727-31. Pubmed: 11398597
  5. 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
  6. 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
  7. Reznek RH, Salway JG, Thomas PK: Plasma-myoinositol concentrations in uraemic neuropathy. Lancet. 1977 Mar 26;1(8013):675-6. Pubmed: 66475
  8. Scully SE, Stebner FC, Yoest SM: Magnetic resonance spectroscopic findings in neuro-Behcet disease. Neurologist. 2004 Nov;10(6):323-6. Pubmed: 15518598
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. Grzelec H: [Pathogenesis and treatment of diabetic neuropathy] Neurol Neurochir Pol. 1991 Jul-Aug;25(4):477-84. Pubmed: 1666426
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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

Enzymes

Gene Name:
GLA
Uniprot ID:
P06280
Reactions
Galactinol + Water unknown Myoinositol + Beta-D-Galactosedetails
Gene Name:
CDIPT
Uniprot ID:
O14735
Reactions
CDP-diacylglycerol + Myoinositol unknown Cytidine monophosphate + phosphatidyl-1D-myo-inositoldetails
CDP-diacylglycerol + Myoinositol unknown Cytidine monophosphate + 1-Phosphatidyl-D-myo-inositoldetails
Gene Name:
MIOX
Uniprot ID:
Q9UGB7
Reactions
Myoinositol + Oxygen unknown D-Glucuronic acid + Waterdetails
Gene Name:
IMPA1
Uniprot ID:
P29218
Reactions
Myo-inositol phosphate + Water unknown Myoinositol + Phosphoric aciddetails
Inositol phosphate + Water unknown Myoinositol + Phosphoric aciddetails
D-Myo-inositol 4-phosphate + Water unknown Myoinositol + Phosphoric aciddetails
Myo-inositol 1-phosphate + Water unknown Myoinositol + Phosphoric aciddetails
Gene Name:
IMPA2
Uniprot ID:
O14732
Reactions
Myo-inositol phosphate + Water unknown Myoinositol + Phosphoric aciddetails
Inositol phosphate + Water unknown Myoinositol + Phosphoric aciddetails
D-Myo-inositol 4-phosphate + Water unknown Myoinositol + Phosphoric aciddetails
Myo-inositol 1-phosphate + Water unknown Myoinositol + Phosphoric aciddetails
Gene Name:
GDE1
Uniprot ID:
Q9NZC3
Reactions
1-(sn-Glycero-3-phospho)-1D-myo-inositol + Water unknown Myoinositol + Glycerol 3-phosphatedetails
Gene Name:
IMPAD1
Uniprot ID:
Q9NX62
Reactions
Myo-inositol phosphate + Water unknown Myoinositol + Phosphoric aciddetails
Inositol phosphate + Water unknown Myoinositol + Phosphoric aciddetails
D-Myo-inositol 4-phosphate + Water unknown Myoinositol + Phosphoric aciddetails
Myo-inositol 1-phosphate + Water unknown Myoinositol + Phosphoric aciddetails