Human Metabolome Database Version 3.5

Showing metabocard for Myoinositol (HMDB00211)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:05 -0700
HMDB ID HMDB00211
Secondary Accession Numbers
  • HMDB02256
Metabolite Identification
Common Name Myoinositol
Description Inositol 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H12O6
Average Molecular Weight 180.1559
Monoisotopic Molecular Weight 180.063388116
IUPAC Name (1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional IUPAC Name myo-inositol
CAS Registry Number 87-89-8
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 Key CDAISMWEOUEBRE-GPIVLXJGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Homomonocyclic Compounds
Class Cyclic Alcohols and Derivatives
Sub Class Cyclitols and Derivatives
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • chiro-inositol(ChEBI)
Substituents
  • 1,2 Diol
  • Cyclohexane
  • Saccharide
  • Secondary Alcohol
  • Sugar Alcohol
Direct Parent Cyclitols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerophospholipid metabolism
  • Component of Inositol phosphate metabolism
  • Component of Streptomycin biosynthesis
  • Osmolyte
  • Second messenger
Application Not Available
Cellular locations
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 225 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 143 mg/mL at 19 °C Human Metabolome Project
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 485 g/L ALOGPS
LogP -2.59 ALOGPS
LogP -3.8 ChemAxon
LogS 0.43 ALOGPS
pKa (strongest acidic) 12.29 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 121.38 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 35.77 ChemAxon
Polarizability 16.14 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-MS
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Neuron
  • Testes
  • Kidney
  • Brain
  • Myelin
  • Prostate
  • Nerve Cells
  • Basal Ganglia
Pathways
Name SMPDB Link KEGG Link
Inositol Metabolism SMP00011 map00562 Link_out
Galactose Metabolism SMP00043 map00052 Link_out
Phosphatidylinositol Phosphate Metabolism SMP00463 map00562 Link_out
Inositol Phosphate Metabolism SMP00462 map00562 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
17.1 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
24.0 +/- 7.8 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
23.0 +/- 8.0 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
30.0 (21.0-49.0) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
174.0 +/- 31.0 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
84 +/- 40 uM Not Specified Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
158.8 +/- 46.07 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
138.3 +/- 24.4 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
133.0 (111.0-155.0) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
12.6 (5.1-15.3) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
18.8 +/- 2.9 umol/mmol creatinine Adult (>18 years old) Not Specified Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
22.4 (7.9-36.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
52.8 +/- 47.7 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
6.11 +/- 6.25 umol/mmol creatinine Infant (0-1 year old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 20.0 (23.0–24.0) uM Adult (>18 years old) Both Ribose-5-phosphate isomerase deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 158.8 +/- 27.2 uM Adult (>18 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 158.8 +/- 27.2 uM Not Specified Not Specified Alzheimer's disease
Urine Detected and Quantified 20.33 +/- 13.70 umol/mmol creatinine Adult (>18 years old) Not Specified Cachexia
Associated Disorders and Diseases
Disease References
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 Link_out
      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 Link_out
          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 Link_out
              Associated OMIM IDs
              • 104300 Link_out (Alzheimer's disease)
              • 608611 Link_out (Ribose-5-phosphate isomerase deficiency)
              DrugBank ID Not Available
              DrugBank Metabolite ID Not Available
              Phenol Explorer Compound ID Not Available
              Phenol Explorer Metabolite ID Not Available
              FoodDB ID FDB010547
              KNApSAcK ID C00001164 Link_out
              Chemspider ID 10239179 Link_out
              KEGG Compound ID C00137 Link_out
              BioCyc ID MYO-INOSITOL Link_out
              BiGG ID 33990 Link_out
              Wikipedia Link MI Link_out
              NuGOwiki Link HMDB00211 Link_out
              Metagene Link HMDB00211 Link_out
              METLIN ID 5221 Link_out
              PubChem Compound Not Available
              PDB ID INS Link_out
              ChEBI ID 17268 Link_out
              References
              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)
              General References
              1. Gryz EA, Galicka-Latala D, Szczudlik A, Sieradzki J: [Etiopathogenesis of diabetic neuropathy] Przegl Lek. 2000;57(12):727-31. Pubmed: 11398597 Link_out
              2. 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 Link_out
              3. 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 Link_out
              4. Reznek RH, Salway JG, Thomas PK: Plasma-myoinositol concentrations in uraemic neuropathy. Lancet. 1977 Mar 26;1(8013):675-6. Pubmed: 66475 Link_out
              5. Scully SE, Stebner FC, Yoest SM: Magnetic resonance spectroscopic findings in neuro-Behcet disease. Neurologist. 2004 Nov;10(6):323-6. Pubmed: 15518598 Link_out
              6. 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 Link_out
              7. 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 Link_out
              8. 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 Link_out
              9. 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 Link_out
              10. 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 Link_out
              11. 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 Link_out
              12. Grzelec H: [Pathogenesis and treatment of diabetic neuropathy] Neurol Neurochir Pol. 1991 Jul-Aug;25(4):477-84. Pubmed: 1666426 Link_out
              13. 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 Link_out
              14. 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 Link_out
              15. 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 Link_out
              16. 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 Link_out
              17. 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 Link_out
              18. 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 Link_out
              19. 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 Link_out
              20. 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 Link_out
              21. 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 Link_out

              Enzymes
              Name: Alpha-galactosidase A
              Reactions:
              Galactinol + Water unknown Myoinositol + Beta-D-Galactose details
              Gene Name: GLA
              Uniprot ID: P06280 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: CDP-diacylglycerol--inositol 3-phosphatidyltransferase
              Reactions:
              CDP-diacylglycerol + Myoinositol unknown Cytidine monophosphate + phosphatidyl-1D-myo-inositol details
              CDP-diacylglycerol + Myoinositol unknown Cytidine monophosphate + 1-Phosphatidyl-D-myo-inositol details
              Gene Name: CDIPT
              Uniprot ID: O14735 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Inositol oxygenase
              Reactions:
              Myoinositol + Oxygen unknown D-Glucuronic acid + Water details
              Gene Name: MIOX
              Uniprot ID: Q9UGB7 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Inositol monophosphatase 1
              Reactions:
              Myo-inositol phosphate + Water unknown Myoinositol + Phosphoric acid details
              Inositol phosphate + Water unknown Myoinositol + Phosphoric acid details
              D-Myo-inositol 4-phosphate + Water unknown Myoinositol + Phosphoric acid details
              Myo-inositol 1-phosphate + Water unknown Myoinositol + Phosphoric acid details
              Gene Name: IMPA1
              Uniprot ID: P29218 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Inositol monophosphatase 2
              Reactions:
              Myo-inositol phosphate + Water unknown Myoinositol + Phosphoric acid details
              Inositol phosphate + Water unknown Myoinositol + Phosphoric acid details
              D-Myo-inositol 4-phosphate + Water unknown Myoinositol + Phosphoric acid details
              Myo-inositol 1-phosphate + Water unknown Myoinositol + Phosphoric acid details
              Gene Name: IMPA2
              Uniprot ID: O14732 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Glycerophosphodiester phosphodiesterase 1
              Reactions:
              1-(sn-Glycero-3-phospho)-1D-myo-inositol + Water unknown Myoinositol + Glycerol 3-phosphate details
              Gene Name: GDE1
              Uniprot ID: Q9NZC3 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Inositol monophosphatase 3
              Reactions:
              Myo-inositol phosphate + Water unknown Myoinositol + Phosphoric acid details
              Inositol phosphate + Water unknown Myoinositol + Phosphoric acid details
              D-Myo-inositol 4-phosphate + Water unknown Myoinositol + Phosphoric acid details
              Myo-inositol 1-phosphate + Water unknown Myoinositol + Phosphoric acid details
              Gene Name: IMPAD1
              Uniprot ID: Q9NX62 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA