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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2017-11-01 18:01:20 UTC
Update Date2019-07-23 14:38:49 UTC
HMDB IDHMDB0240209
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-chiro-Inositol
DescriptionD-chiro-Inositol (also known as 1D-chiro-inositol, abbreviated DCI) 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 exactly 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. myo-Inositol is converted into DCI by an insulin dependent NAD/NADH epimerase enzyme. It is known to be an important secondary messenger in insulin signal transduction. DCI accelerates the dephosphorylation of glycogen synthase and pyruvate dehydrogenase, rate limiting enzymes of non-oxidative and oxidative glucose disposal. DCI may act to bypass defective normal epimerization of myo-inositol to DCI associated with insulin resistance and at least partially restore insulin sensitivity and glucose disposal.
Structure
Data?1563892729
Synonyms
ValueSource
(+)-InositolChEBI
(1R,2R,3S,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexolChEBI
1,2,4/3,5,6-cyclohexanehexolChEBI
cis-1,2,4-trans-3,5,6-CyclohexanehexolChEBI
D-InositolChEBI
DCIChEBI
(+)-chiro-InositolHMDB
1D-chiro-inositolHMDB
D-(+)-chiro-InositolHMDB
D-chiro-InositolHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
Traditional NameD-chiro-inositol
CAS Registry Number643-12-9
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+/m0/s1
InChI KeyCDAISMWEOUEBRE-LKPKBOIGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclohexanols. These 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
Polarizability16.1 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
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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001138
KNApSAcK IDNot Available
Chemspider ID10254647
KEGG Compound IDC19891
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27372
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available