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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-01 17:50:48 UTC
Update Date2019-11-07 17:33:39 UTC
HMDB IDHMDB0240207
Secondary Accession NumbersNone
Metabolite Identification
Common Nameepi-Inositol
Descriptionepi-Inositol, also known as cocositol or quercinitol, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. epi-Inositol is an inositol isoform. epi-Inositol is an extremely weak basic (essentially neutral) compound (based on its pKa). 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. Scyllitol was found to reverse memory deficits in the mice, reduce the amount of Aβ plaque in the brains of the mice, and reversed other symptoms associated with the presence of Aβ in the brain (PMID: 16767098 ). Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. Results reported by Viola et al (PMID: 15340856 ) suggest that high CSF concentrations of scyllo-inositol can be induced by chronic alcoholism. It was first isolated from the kidneys of fish in 1858 by Staedeler and Freierchs. It has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379). Scyllitol is a naturally occurring plant sugar alcohol found most abundantly in the coconut palm. Scyllitol is an isomer of cyclohexanehexol or inositol.
Structure
Data?1573148018
Synonyms
ValueSource
(1R,2R,3R,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexolChEBI
1,2,3,4,5/6-cyclohexanehexolChEBI
(1R,2R,3R,4R,5R,6R)-Cyclohexane-1,2,3,4,5,6-hexolHMDB
1,3,5/2,4,6-cyclohexanehexolHMDB
CocositolHMDB
Cyclohexane-1,2,3,4,5,6-hexolHMDB
QuercinitolHMDB
Epi-inositolHMDB
epi-CyclohexanehexolHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional Name(+)-inositol
CAS Registry Number488-58-4
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-NIPYSYMMSA-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
Not 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
Refractivity35.78 m³·mol⁻¹ChemAxon
Polarizability16.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-9700000000-6cc8567e1b238f96f926Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-00fr-9001040000-00e67b437c4329aee95dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000b-9700000000-330e2df8df8562e944f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9100000000-126dbfb7ce2da687d09fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4j-9000000000-c5c2ae010c0a31be06f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-7c41046f5cd7ac51aedaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-43d319e5d29dbbb36c38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gl-8900000000-829257b7deb866db4ef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-6d453252588a04df8624Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-749e1b0857cad96ba8a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9200000000-7201474b84312a32a966Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10254648
KEGG Compound IDNot Available
BioCyc IDCPD-8059
BiGG IDNot Available
Wikipedia LinkEpi-Inositol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID23927
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available