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Record Information
Version1.0
Creation Date2016-09-30 22:26:46 UTC
Update Date2020-06-04 20:52:02 UTC
BMDB IDBMDB0000211
Secondary Accession Numbers
  • BMDB00211
Metabolite Identification
Common NameMyoinositol
DescriptionMyoinositol, also known as inosite or MI, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Myoinositol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Myoinositol exists in all living species, ranging from bacteria to humans. In cattle, myoinositol is involved in the metabolic pathway called the inositol phosphate metabolism pathway. Myoinositol has been found to be associated with several diseases known as cachexia, eosinophilic esophagitis, colorectal cancer, and schizophrenia; also myoinositol has been linked to the inborn metabolic disorders including ribose-5-phosphate isomerase deficiency.
Structure
Thumb
Synonyms
ValueSource
(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
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number87-89-8
SMILESNot Available
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-GPIVLXJGSA-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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Myelin sheath
Biospecimen Locations
  • Basal Ganglia
  • Blood
  • Brain
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Mammary Gland
  • Milk
  • Neuron
  • Placenta
  • Prostate Tissue
  • Semen
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Basal GangliaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected and Quantified45 +/- 11 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified1177 +/- 221 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified504 +/- 133 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified588.379 +/- 55.507 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified227.581 +/- 55.507 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified222.0299 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified116.566 +/- 15.542 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified183.175 (122.116-205.378) uMNot SpecifiedNot Specified
Normal
    • Esperanza Troyano...
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Semimembranosus MuscleDetected and Quantified593 +/- 126 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified7193 +/- 1232 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Treated with growth-promoting hormones
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Mycobacterium avium subsp. paratuberculosis infection
details
HMDB IDHMDB0000211
DrugBank IDDB13178
Phenol Explorer Compound IDNot Available
FooDB IDFDB010547
KNApSAcK IDC00001164
Chemspider ID10239179
KEGG Compound IDC00137
BioCyc IDMYO-INOSITOL
BiGG ID33990
Wikipedia LinkInositol
METLIN ID5221
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17268
References
Synthesis ReferenceIselin, Beat M. Synthesis of inositol-5-monophosphoric acid and scyllitol monophosphoric acid. Journal of the American Chemical Society (1949), 71 3822-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.

Enzymes

General function:
Involved in inositol oxygenase activity
Specific function:
Not Available
Gene Name:
MIOX
Uniprot ID:
A7MBE4
Molecular weight:
32973.0
Reactions
Myoinositol + Oxygen → D-Glucuronic acid + Waterdetails
General function:
Replication, recombination and repair
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate), suggesting that it may play a role in signal transduction. Also able to catalyze the hydrolysis of dinucleoside oligophosphates, with Ap6A and Ap5A being the preferred substrates. The major reaction products are ADP and p4a from Ap6A and ADP and ATP from Ap5A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT11
Uniprot ID:
Q58CW0
Molecular weight:
18519.0
General function:
Carbohydrate transport and metabolism
Specific function:
Responsible for the provision of inositol required for synthesis of phosphatidylinositol and polyphosphoinositides and has been implicated as the pharmacological target for lithium action in brain. Has broad substrate specificity and can use myo-inositol monophosphates, myo-inositol 1,3-diphosphate, myo-inositol 1,4-diphosphate, scyllo-inositol-phosphate, glucose-1-phosphate, glucose-6-phosphate, fructose-1-phosphate, beta-glycerophosphate, and 2'-AMP as substrates (By similarity). Is equally active with myo-inositol monophosphate and D-galactose 1-phosphate.
Gene Name:
IMPA1
Uniprot ID:
P20456
Molecular weight:
30056.0
Reactions
Myo-inositol 1-phosphate + Water → Myoinositol + Hydrogen phosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Exhibits 3'-nucleotidase activity toward adenosine 3',5'-bisphosphate (PAP), namely hydrolyzes adenosine 3',5'-bisphosphate into adenosine 5'-monophosphate (AMP) and a phosphate. May play a role in the formation of skeletal elements derived through endochondral ossification, possibly by clearing adenosine 3',5'-bisphosphate produced by Golgi sulfotransferases during glycosaminoglycan sulfation. Has no activity toward 3'-phosphoadenosine 5'-phosphosulfate (PAPS) or inositol phosphate (IP) substrates including I(1)P, I(1,4)P2, I(1,3,4)P3, I(1,4,5)P3 and I(1,3,4,5)P4.
Gene Name:
IMPAD1
Uniprot ID:
Q2KJ53
Molecular weight:
38924.0
General function:
Energy production and conversion
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Hydrolyzes lysoglycerophospholipids to produce lysophosphatidic acid (LPA) and the corresponding amines. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q3T0T0
Molecular weight:
37653.0
General function:
Replication, recombination and repair
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate) and [PP]2-InsP4 (bisdiphosphoinositol tetrakisphosphate), suggesting that it may play a role in signal transduction. InsP6 (inositol hexakisphosphate) is not a substrate. Also able to catalyze the hydrolysis of dinucleoside oligophosphates, with Ap6A and Ap5A being the preferred substrates. The major reaction products are ADP and p4a from Ap6A and ADP and ATP from Ap5A. Also able to hydrolyze 5-phosphoribose 1-diphosphate (By similarity).
Gene Name:
NUDT3
Uniprot ID:
A2VE79
Molecular weight:
19362.0
General function:
Involved in sodium ion binding
Specific function:
Involved in the sodium-dependent cotransport of myo-inositol (MI) with a Na(+):MI stoichiometry of 2:1. Exclusively responsible for apical MI transport and absorption in intestine. Also can transport D-chiro-inositol (DCI) but not L-fructose. Exhibits stereospecific cotransport of both D-glucose and D-xylose. May induce apoptosis through the TNF-alpha, PDCD1 pathway. May play a role in the regulation of MI concentration in serum, involving reabsorption in at least the proximal tubule of the kidney.
Gene Name:
SLC5A11
Uniprot ID:
Q3ZC26
Molecular weight:
73957.0
General function:
Involved in transporter activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
O19135
Molecular weight:
79621.0