INOSITOL (CED0000809)

Record Information
Version1.0
Creation Date2016-05-19 02:10:05 UTC
Update Date2026-05-14 19:30:50 UTC
Accession NumberCHEM006107
Identification
Common NameINOSITOL
ClassSmall Molecule
Description
INOSITOL (C6H12O6) is an organic compound with an average molecular weight of 180.16 g/mol. INOSITOL belongs to the alcohols and polyols, a subclass of organooxygen compounds within the organic compounds. Industrially, it is used as a humectant, anti-static agent, softener, conditioner, and as a flavouring and nutrient; it also serves as an environmental nutrient (PMC10372128). This compound is found in or released from 29 recorded sources, including vitamins in healthcare, pharmaceuticals, and veterinary products; fermentation processes for beer, food preservation, molasses and treatment of molasses, and the preparation of malt and vinegar in food, food processing, and cookware; bleaching agents, cigar cigarettes, non electric simulated smoking devices, pipe accessories, and perfumes within detergents and soaps in household cleaning and consumer products; and antennas, electrodes, electric switches, electrically stimulated smoking devices, conductors or conductive bodies characterised by the conductive materials, and five other sources in electrical and electronic equipment. Recorded exposure routes include oral, intramuscular, and vaginal administration. At the molecular level, inositol acts as an inhibitor of the Amyloid-beta precursor protein (APP). Regarding health effects, the compound is associated with neurodegenerative disease (PMC6378111) and is found at increased levels in the blood of individuals with low birth weight (PMC7235385). In a therapeutic context, inositol is used as a treatment for anxiety and depression (PMC8746988) and has a therapeutic effect on infertility (PMC9476395).
Contaminant TypeNot Available
Chemical Structure
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
Iso-inositolHMDB
MIHMDB
MyoinositeHMDB
PhaseomanniteHMDB
Rat antispectacled eye factorHMDB
Myo inositolHMDB
Vitamin b8HMDB
Myo-inositolHMDB
Chemical FormulaC6H12O6
Average Molecular Mass180.156 g/mol
Monoisotopic Mass180.063 g/mol
CAS Registry Number87-89-8
IUPAC Name(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional NameL-inositol
SMILESO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O
InChI IdentifierInChI=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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 Area121.38 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-014j-0953000000-1571a0577293e96091b1Not AvailableView Spectrum
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GC-MSGC-MS Spectrumsplash10-00kb-0942000000-b78076224adf13bade25Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-8942000000-f5d7abd38d6ff547a0a9Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-066r-0975000000-df7304c12b6c9bdb0f76Not AvailableView Spectrum
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LC-MS/MSLC-MS/MS Spectrumsplash10-0a59-3900000000-96084971c3e13a1e7451Not AvailableView Spectrum
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LC-MS/MSLC-MS/MS Spectrumsplash10-0a59-8900000000-cb2e1ff0611a81fa17e4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-9500000000-9196dfc83f5169835173Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9200000000-ed0b6328711fcc006b75Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f89-9100000000-b7e563eb625a43eff7daNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-5900000000-eb20a4cbe497d9962013Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-5cb39f92646251665ebfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-2aeb7708f31c772e2d95Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08gi-8900000000-74f89711a1c6891808a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-8b68ff47f846a8ca1dddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1900000000-03ef8572289795275d9cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0570-9300000000-950a37bd331028801e9fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-c98742ed2c27fed8805bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0570-9700000000-4e8df481dc1f1c124743Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-ea5996664694b27554a8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-a3b1806f4d2d4bc9e470Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-9500000000-40e1f34ad1ad2b894cd9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-9000000000-5d72027b1e4acffd4c29Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, experimental)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, experimental)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6882.0Log mg/kg[3900:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
low birth weightelevated_in_blood_inincreasePMC7235385
infertilityhas_therapeutic_effect_onNot AvailablePMC9476395
anxietyis_treatment_forNot AvailablePMC8746988
depressionis_treatment_forNot AvailablePMC8746988
neurodegenerative diseaseassociated_withNot AvailablePMC6378111
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
265VitaminsHealthcare, pharmaceuticals & veterinary productsNot Available
490Personal care & cosmeticsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
8 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureNeutral alpha-glucosidase CQ8TET4HumansPredicted (SEA)0.934191
Click to view 3D structureAlpha-galactosidase AD3ZJF9Rattus norvegicusPredicted (SEA)0.934191
Click to view 3D structureLysosomal alpha-glucosidaseQ6P7A9Rattus norvegicusPredicted (SEA)3.50322
Maltase-glucoamylase structureClick to view 3D structureMaltase-glucoamylaseO43451HumansPredicted (SEA)4.35956
Click to view 3D structureLysosomal acid glucosylceramidaseP17439Mus musculusPredicted (SEA)0.0778492
Lysosomal acid glucosylceramidase structureClick to view 3D structureLysosomal acid glucosylceramidaseP04062HumansPredicted (SEA)8.64126
Click to view 3D structureGlucoamylase, intracellular sporulation-specificP08019Saccharomyces cerevisiae S288cPredicted (SEA)2.10193
Click to view 3D structureInositol 1,4,5-trisphosphate-gated calcium channel ITPR3Q8WN95Bos taurusPredicted (SEA)1.08989
Click to view 3D structureAlpha-glucosidase MAL62P07265Saccharomyces cerevisiaePredicted (SEA)2.25763
Tissue alpha-L-fucosidase structureClick to view 3D structureTissue alpha-L-fucosidaseP04066HumansPredicted (SEA)3.03612
Click to view 3D structurePlasma alpha-L-fucosidaseQ9BTY2HumansPredicted (SEA)1.79053
Click to view 3D structureMannosyl-oligosaccharide alpha-1,2-mannosidase isoform BP53624Drosophila melanogasterPredicted (SEA)0.0778492
Click to view 3D structureBeta-galactosidaseD3ZUM4Rattus norvegicusPredicted (SEA)2.25763
Click to view 3D structureNeutral alpha-glucosidase CQ8BVW0Mus musculusPredicted (SEA)2.41333
Click to view 3D structureSucrase-isomaltase, intestinalP23739Rattus norvegicusPredicted (SEA)8.79696
Lysosomal alpha-glucosidase structureClick to view 3D structureLysosomal alpha-glucosidaseP10253HumansPredicted (SEA)8.56341
Click to view 3D structureLactase/phlorizin hydrolaseQ02401Rattus norvegicusPredicted (SEA)3.03612
Click to view 3D structureInositol-trisphosphate 3-kinase AP17105Rattus norvegicusPredicted (SEA)1.32344
Click to view 3D structureLectinB4EH87Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))Predicted (SEA)21.2528
Click to view 3D structureGlycogen debranching enzymeP35574Oryctolagus cuniculusPredicted (SEA)3.26967
Click to view 3D structureTissue alpha-L-fucosidaseP17164Rattus norvegicusPredicted (SEA)2.25763
Click to view 3D structureAlpha-galactosidaseQ42656Coffea arabicaPredicted (SEA)9.10836
Click to view 3D structureBeta-galactosidaseQ58D55Bos taurusPredicted (SEA)13.6236
Click to view 3D structureTissue alpha-L-fucosidaseQ2KIM0Bos taurusPredicted (SEA)2.02408
Click to view 3D structureGlycogen debranching enzymeP35573HumansPredicted (SEA)5.99439
Concentrations
Not Available
External Links
DrugBank IDDB13178
HMDB IDHMDB0000211
FooDB IDFDB010547
Phenol Explorer IDNot Available
KNApSAcK IDC00001164
BiGG ID33990
BioCyc IDMYO-INOSITOL
METLIN ID5221
PDB IDNot Available
Wikipedia LinkInositol
Chemspider ID10239179
ChEBI ID17268
PubChem Compound IDNot Available
Kegg Compound IDC00137
YMDB IDYMDB00173
ECMDB IDECMDB04087
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Iselin, Beat M. Synthesis of inositol-5-monophosphoric acid and scyllitol monophosphoric acid. Journal of the American Chemical Society (1949), 71 3822-5.
2. Gryz EA, Galicka-Latala D, Szczudlik A, Sieradzki J: [Etiopathogenesis of diabetic neuropathy]. Przegl Lek. 2000;57(12):727-31.
3. Kim MO, Im JH, Choi CG, Lee MC: Proton MR spectroscopic findings in paroxysmal kinesigenic dyskinesia. Mov Disord. 1998 May;13(3):570-5.
4. Wuarin-Bierman L, Zahnd GR: Current aspects of research on the pathogenesis of diabetic neuropathy. Diabete Metab. 1986 Dec;12(6):319-24.
5. Reznek RH, Salway JG, Thomas PK: Plasma-myoinositol concentrations in uraemic neuropathy. Lancet. 1977 Mar 26;1(8013):675-6.
6. Scully SE, Stebner FC, Yoest SM: Magnetic resonance spectroscopic findings in neuro-Behcet disease. Neurologist. 2004 Nov;10(6):323-6.
7. 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.
8. 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.
9. 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.
10. 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.
11. Servo C, Pitkanen E: Variation in polyol levels in cerebrospinal fluid and serum in diabetic patients. Diabetologia. 1975 Dec;11(6):575-80.
12. 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.
13. Grzelec H: [Pathogenesis and treatment of diabetic neuropathy]. Neurol Neurochir Pol. 1991 Jul-Aug;25(4):477-84.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
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.
22. 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.
23. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=11034685
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=11244303
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=11323092
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=11772411
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=12478879
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=12832083
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=14583919
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=14681857
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=15181167
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=15295080
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=15558078
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=16410747
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=1694860
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=17722064
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=18650262
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=18854045
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=19097871
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=19383710
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=22285975
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=22461977
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=22517104
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=838172