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Myo-Inositol (FDB010547)

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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
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
Predicted GC-MSMyo-Inositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMyo-Inositol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a59-3900000000-96084971c3e13a1e74512012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-1de17d7f53ca727e6d722012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0zh9-9000000000-bef910214341056a78aa2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-41a49af846b1636763b52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-06f9ecfccf30d40ef2042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-004i-0900000000-bca88f6782a8ed3862232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-004i-1900000000-500ab195d69568b8678b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-01ti-5900000000-a1657b54c985e2be1d192020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-000i-9600000000-325cbb8dbfdeafb2b31f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-9200000000-9145a4766351204e723a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-000i-9100000000-2bbbcfa4733b749ec7682020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-000i-9000000000-de0ec8731a152b612bb92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-0079-9000000000-41d049d1feef94e190d42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-059i-9000000000-796e728daf28d5122dee2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-059i-9000000000-8643e206319f3008a8d42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0abi-9000000000-98e61f19bc2842f2e97b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0ab9-9000000000-29aa062fc4d5341167b62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-03di-1900000000-5a2897fd032a959918b32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000i-9000000000-71c4786b7034d5a0a0a92020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5cb39f92646251665ebf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2aeb7708f31c772e2d952016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8900000000-74f89711a1c6891808a42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8b68ff47f846a8ca1ddd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-03ef8572289795275d9c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-9300000000-950a37bd331028801e9f2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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.