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Showing Compound Chiro-Inositol (FDB001138)

Record Information
Version1.0
Creation date2010-04-08 22:04:51 UTC
Update date2020-09-17 15:30:59 UTC
Primary IDFDB001138
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChiro-Inositol
DescriptionLevoinositol (also known as 1L-chiro-Inositol or L-chiro-inositol, abbreviated LCI) 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, with 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. Levoinositol is found in dandelion and is widely distributed in higher plants predominantly as its monomethyl ether. 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 chiro-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 Number643-12-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Polarizability16.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H12O6
IUPAC name(1R,2R,3S,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+/m0/s1
InChI KeyCDAISMWEOUEBRE-LKPKBOIGSA-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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSChiro-Inositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dr-9700000000-6cc8567e1b238f96f926Spectrum
Predicted GC-MSChiro-Inositol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9001040000-00e67b437c4329aee95dSpectrum
Predicted GC-MSChiro-Inositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5cb39f92646251665ebf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2aeb7708f31c772e2d952016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8900000000-74f89711a1c6891808a42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8b68ff47f846a8ca1ddd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-03ef8572289795275d9c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-9300000000-950a37bd331028801e9f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-c98742ed2c27fed8805b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0570-9700000000-4e8df481dc1f1c1247432021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ea5996664694b27554a82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-a3b1806f4d2d4bc9e4702021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-9500000000-40e1f34ad1ad2b894cd92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-5d72027b1e4acffd4c292021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBTS07-E:BTS07-E
EAFUS IDNot Available
Dr. Duke IDCHIRO-INOSITOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Carob100.000 - 100.000 mg/100 g100.000 mg/100 gDUKE
Soy beanExpected but not quantifiedNot AvailableDUKE
Showing 1 to 2 of 2 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).