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Record Information
Version1.0
Creation Date2016-07-13 19:42:17 UTC
Update Date2016-08-01 19:10:38 UTC
LmdbLMDB00097
Secondary Accession NumbersNone
Metabolite Identification
Common NameMyoinositol
Descriptionmyo-Inositol, also known as bios I or cyclohexitol, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. myo-Inositol is an extremely weak basic (essentially neutral) compound (based on its pKa). An inositol having myo- configuration. myo-Inositol exists in all living species, ranging from bacteria to humans. Within humans, myo-inositol participates in a number of enzymatic reactions. In particular, myo-inositol can be biosynthesized from D-myo-inositol 4-phosphate through its interaction with the enzyme inositol monophosphatase 1. In addition, myo-inositol can be biosynthesized from myo-inositol 1-phosphate through its interaction with the enzyme inositol monophosphatase 1. In humans, myo-inositol is involved in inositol metabolism. Outside of the human body, myo-Inositol is found, on average, in the highest concentration within a few different foods, such as carobs, apples, and cottonseeds and in a lower concentration in lentils, milk (cow), and asparagus. myo-Inositol has also been detected, but not quantified in, several different foods, such as globe artichokes, corn salad, herbs and spices, arrowhead, and red rices. This could make myo-inositol a potential biomarker for the consumption of these foods. myo-Inositol, with regard to humans, has been found to be associated with several diseases such as cachexia, uremia, schizophrenia, and eosinophilic esophagitis; myo-inositol has also been linked to the inborn metabolic disorder ribose-5-phosphate isomerase deficiency.
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
Iso-inositolHMDB
MIHMDB
MyoinositeHMDB
PhaseomanniteHMDB
Rat antispectacled eye factorHMDB
Myo inositolHMDB
Vitamin b8HMDB
Myo-inositolHMDB
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 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
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-014j-0953000000-1571a0577293e96091b1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-00kb-0932000000-96ddc21293431d746ad2Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0942000000-b78076224adf13bade25Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0942000000-42c4e40d04b4f306535dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-00di-8942000000-f5d7abd38d6ff547a0a9Spectrum
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-066r-0975000000-df7304c12b6c9bdb0f76Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-0953000000-1571a0577293e96091b1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0932000000-96ddc21293431d746ad2Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0942000000-b78076224adf13bade25Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8942000000-f5d7abd38d6ff547a0a9Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066r-0975000000-df7304c12b6c9bdb0f76Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-9700000000-18a13ab4150e6ebb20cdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-00fr-9001040000-00e67b437c4329aee95dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a59-3900000000-96084971c3e13a1e7451Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-1de17d7f53ca727e6d72Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0zh9-9000000000-bef910214341056a78aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-41a49af846b1636763b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-06f9ecfccf30d40ef204Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-004i-0900000000-bca88f6782a8ed386223Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-004i-1900000000-500ab195d69568b8678bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-01ti-5900000000-a1657b54c985e2be1d19Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-000i-9600000000-325cbb8dbfdeafb2b31fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-9200000000-9145a4766351204e723aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-000i-9100000000-2bbbcfa4733b749ec768Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-000i-9000000000-de0ec8731a152b612bb9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-0079-9000000000-41d049d1feef94e190d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-059i-9000000000-796e728daf28d5122deeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-059i-9000000000-8643e206319f3008a8d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0abi-9000000000-98e61f19bc2842f2e97bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0ab9-9000000000-29aa062fc4d5341167b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-03di-1900000000-5a2897fd032a959918b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000i-9000000000-71c4786b7034d5a0a0a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5cb39f92646251665ebfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2aeb7708f31c772e2d95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8900000000-74f89711a1c6891808a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8b68ff47f846a8ca1dddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-03ef8572289795275d9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-9300000000-950a37bd331028801e9fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Brain
  • Cerebrospinal Fluid (CSF)
  • Kidney
  • Lung
  • Milk
  • Plasma
  • Serum
  • Urine
  • Vitreous Humour
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
BrainDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableNot AvailableOvine details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LungDetected and Quantified3.5+/-0.2 umol/gNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified0.00375 +/- 0.000688 uMNot AvailablePorcine details
SerumDetected and Quantified0.00259 +/- 0.000572 uMNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Vitreous HumourDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
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
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available