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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:26 UTC
NP-MRD IDNP0000748
Secondary Accession NumbersNone
Natural Product Identification
Common Namemyo-Inositol
DescriptionMyo-Inositol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, of which cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol is the most widely occurring form in nature. The other known inositols include scyllo-inositol, muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol and cis-inositol. Myo-Inositol is found naturally in many foods (particularly in cereals with high bran content) and can be used as a sweetner as it has half the sweetness of sucrose (table sugar). Myo-Inositol was once considered a member of the vitamin B complex and given the name: Vitamin B8. However, because it is produced by the human body from glucose, it is not an essential nutrient, and therefore cannot be called a vitamin. Myo-Inositol is a precursor molecule for a number of secondary messengers including various inositol phosphates. In addition, inositol/myo-inositol is an important component of the lipids known as phosphatidylinositol (PI) phosphatidylinositol phosphate (PIP). Myo-Inositol is synthesized from glucose, via glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerised by an inositol-3-phosphate synthase enzyme to myo-inositol 1-phosphate, which is then dephosphorylated by an inositol monophosphatase enzyme to give free myo-inositol. In humans, myo-inositol is primarily synthesized in the kidneys at a rate of a few grams per day. Myo-Inositol can be used in the management of preterm babies who have or are at a risk of infant respiratory distress syndrome. It is also used as a treatment for polycystic ovary syndrome (PCOS). It works by increasing insulin sensitivity, which helps to improve ovarian function and reduce hyperandrogenism. Reduced levels of myo-inositol have been found in the spinal fluid of depressed patients and levels are significantly reduced in brain samples of suicide victims.
Structure
Thumb
Synonyms
ValueSource
(1R,2R,3S,4S,5R,6S)-Cyclohexane-1,2,3,4,5,6-hexolChEBI
1,2,3,4,5,6-HEXAHYDROXY-cyclohexaneChEBI
1,2,3,5/4,6-cyclohexanehexolChEBI
1D-Myo-inositolChEBI
1l-Myo-inositolChEBI
Bios IChEBI
cis-1,2,3,5-trans-4,6-CyclohexanehexolChEBI
CyclohexitolChEBI
D-Myo-inositolChEBI
DamboseChEBI
I-inositolChEBI
InositeChEBI
InositolChEBI
InsChEBI
L-Myo-inositolChEBI
Meat sugarChEBI
Meso-inositolChEBI
MyoinositolChEBI
InositalKegg
Myo inositolHMDB
Vitamin B8HMDB
Myo-inositolHMDB
iso-InositolHMDB
MIHMDB
MyoinositeHMDB
PhaseomanniteHMDB
Rat antispectacled eye factorHMDB
Chemical FormulaC6H12O6
Average Mass180.1559 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional NameL-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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-11View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaKNApSAcK Database
Averrhoa carambolaKNApSAcK Database
Brassica oleracea var. italicaKNApSAcK Database
Carica papayaKNApSAcK Database
Centrosema pubescensKNApSAcK Database
Citrus sinensisKNApSAcK Database
Coffea arabicaKNApSAcK Database
Curcuma domesticaKNApSAcK Database
Dalbergia sissooKNApSAcK Database
Daucus carotaKNApSAcK Database
Desmodium intortumKNApSAcK Database
Desmodium uncinatumKNApSAcK Database
Lablab purpureusKNApSAcK Database
Lens culinarisKNApSAcK Database
Liriodendron tulipiferaKNApSAcK Database
Lotononis angolensisKNApSAcK Database
Lotononis bainesiiKNApSAcK Database
Macroptilium atropurpureumKNApSAcK Database
Macroptilium bracteatumKNApSAcK Database
Macroptilium lathyroidesKNApSAcK Database
Macrotyloma axillareKNApSAcK Database
Macrotyloma uniflorumKNApSAcK Database
Marsdenia tomentosaKNApSAcK Database
Medicago sativaKNApSAcK Database
Murraya paniculataKNApSAcK Database
Oryza sativaKNApSAcK Database
Panax ginsengKNApSAcK Database
Phaseolus vulgarisKNApSAcK Database
Populus maximowicziiKNApSAcK Database
Populus nigraKNApSAcK Database
Prunus aviumKNApSAcK Database
Pueraria PhaseoloidesKNApSAcK Database
Rhodiola kirilowiiKNApSAcK Database
Rhodiola roseaKNApSAcK Database
Rhynchosia beddomeiKNApSAcK Database
Rhynchosia hirtaKNApSAcK Database
Sebertia acuminataKNApSAcK Database
Solanum lycopersicum L.KNApSAcK Database
Solanum tuberosumKNApSAcK Database
Spinacia oleraceaKNApSAcK Database
Stylosanthes guianensisKNApSAcK Database
Stylosanthes humilisKNApSAcK Database
Triticum aestivumKNApSAcK Database
Xylopia poilaneiKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Phoma medicaginisKNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225 °CNot Available
Boiling Point339.10 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility143 mg/mL at 19 °CHuman Metabolome Project
LogP1.680The Good Scents Company Information System
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
Refractivity35.78 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0000211
DrugBank IDDB13178
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010547
KNApSAcK IDC00001164
Chemspider ID10239179
KEGG Compound IDC00137
BioCyc IDMYO-INOSITOL
BiGG IDNot Available
Wikipedia LinkInositol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17268
Good Scents IDrw1251521
References
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. doi: 10.1038/nature07762. [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 ]