Record Information
Version1.0
Creation date2010-04-08 22:09:11 UTC
Update date2020-09-17 15:30:59 UTC
Primary IDFDB010547
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. In humans, most inositol is synthesized in the kidneys, typically in amounts of a few grams per day. It is found in many foods, particularly in cereals with high bran content. It is an isomer of glucose that has traditionally been a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in humans. Inositol is a cyclic polyalcohol that plays an important role as a second messenger in a cell, in the form of inositol phosphates. Inositol phospholipids are important in signal transduction. A possible health effect of inositols, including myo-inositol, was recently reviewed. The review concluded that myo-inositol, together with chiro-inositol, at a 40:1 ratio, were an important therapeutic strategy for the improvement of metabolic, hormonal, and reproductive aspects of polycystic ovarian syndrome (PMID: 29309199).
CAS Number87-89-8
Structure
Thumb
Synonyms
SynonymSource
(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
(1a,2a,3a,4b,5a,6b)-Cyclohexanehexoldb_source
1,2,3,5/4,6-Inositoldb_source
1D-myo-InositolChEBI
1L-myo-InositolChEBI
D-myo-InositolChEBI
i-Inositoldb_source
L-myo-InositolChEBI
meso-Inositoldb_source
Nucitoldb_source
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
Refractivity35.77 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H12O6
IUPAC name(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
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
Isomeric SMILESO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.00%; H 6.71%; O 53.28%DFC
Melting PointMp 225°DFC
Boiling PointNot Available
Experimental Water Solubility143 mg/mL at 19 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMyo-Inositol, 6 TMS, GC-MS Spectrumsplash10-014j-0953000000-1571a0577293e96091b1Spectrum
GC-MSMyo-Inositol, 6 TMS, GC-MS Spectrumsplash10-00kb-0932000000-96ddc21293431d746ad2Spectrum
GC-MSMyo-Inositol, non-derivatized, GC-MS Spectrumsplash10-00kb-0942000000-b78076224adf13bade25Spectrum
GC-MSMyo-Inositol, non-derivatized, GC-MS Spectrumsplash10-00kb-0942000000-42c4e40d04b4f306535dSpectrum
GC-MSMyo-Inositol, 6 TMS, GC-MS Spectrumsplash10-00di-8942000000-f5d7abd38d6ff547a0a9Spectrum
GC-MSMyo-Inositol, 6 TMS, GC-MS Spectrumsplash10-066r-0975000000-df7304c12b6c9bdb0f76Spectrum
GC-MSMyo-Inositol, non-derivatized, GC-MS Spectrumsplash10-014j-0953000000-1571a0577293e96091b1Spectrum
GC-MSMyo-Inositol, non-derivatized, GC-MS Spectrumsplash10-00kb-0932000000-96ddc21293431d746ad2Spectrum
GC-MSMyo-Inositol, non-derivatized, GC-MS Spectrumsplash10-00kb-0942000000-b78076224adf13bade25Spectrum
GC-MSMyo-Inositol, non-derivatized, GC-MS Spectrumsplash10-00di-8942000000-f5d7abd38d6ff547a0a9Spectrum
GC-MSMyo-Inositol, non-derivatized, GC-MS Spectrumsplash10-066r-0975000000-df7304c12b6c9bdb0f76Spectrum
Predicted GC-MSMyo-Inositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dr-9700000000-18a13ab4150e6ebb20cdSpectrum
Predicted GC-MSMyo-Inositol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9001040000-00e67b437c4329aee95dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a59-3900000000-96084971c3e13a1e7451Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-1de17d7f53ca727e6d72Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0zh9-9000000000-bef910214341056a78aaSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-41a49af846b1636763b5Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-06f9ecfccf30d40ef204Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-004i-0900000000-bca88f6782a8ed386223Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-004i-1900000000-500ab195d69568b8678bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-01ti-5900000000-a1657b54c985e2be1d19Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-000i-9600000000-325cbb8dbfdeafb2b31fSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-9200000000-9145a4766351204e723aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-000i-9100000000-2bbbcfa4733b749ec768Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-000i-9000000000-de0ec8731a152b612bb9Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-0079-9000000000-41d049d1feef94e190d4Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-059i-9000000000-796e728daf28d5122deeSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-059i-9000000000-8643e206319f3008a8d4Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0abi-9000000000-98e61f19bc2842f2e97bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0ab9-9000000000-29aa062fc4d5341167b6Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-03di-1900000000-5a2897fd032a959918b3Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000i-9000000000-71c4786b7034d5a0a0a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5cb39f92646251665ebfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2aeb7708f31c772e2d95Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8900000000-74f89711a1c6891808a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8b68ff47f846a8ca1dddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-03ef8572289795275d9cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-9300000000-950a37bd331028801e9fSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID10239179
ChEMBL IDCHEMBL1222251
KEGG Compound IDC00137
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID17268
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00211
CRC / DFC (Dictionary of Food Compounds) IDFCS22-I:FCS22-I
EAFUS ID1795
Dr. Duke IDMYO-INOSITOL|INOSITOL|MESO-INOSITOL
BIGG ID33990
KNApSAcK IDC00001164
HET IDINS
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDInositol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti alopecic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cirrhotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neuropathicDUKE
cholesterolyticDUKE
lipotropicDUKE
sweetener50505 Substance that sweeten food, beverages, medications, etc.DUKE
ubiquiotDUKE
Enzymes
NameGene NameUniProt ID
Alpha-galactosidase AGLAP06280
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043 map00052
Inositol MetabolismSMP00011 map00562
Inositol Phosphate MetabolismSMP00462 map00562
Phosphatidylinositol Phosphate MetabolismSMP00463 map00562
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.