| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:26:46 UTC |
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| Update Date | 2020-06-04 20:52:02 UTC |
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| BMDB ID | BMDB0000211 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Myoinositol |
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| Description | Myoinositol, 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (1R,2R,3S,4S,5R,6S)-Cyclohexane-1,2,3,4,5,6-hexol | ChEBI | | 1,2,3,4,5,6-HEXAHYDROXY-cyclohexane | ChEBI | | 1,2,3,5/4,6-cyclohexanehexol | ChEBI | | 1D-Myo-inositol | ChEBI | | 1l-Myo-inositol | ChEBI | | Bios I | ChEBI | | cis-1,2,3,5-trans-4,6-Cyclohexanehexol | ChEBI | | Cyclohexitol | ChEBI | | D-Myo-inositol | ChEBI | | Dambose | ChEBI | | I-inositol | ChEBI | | Inosite | ChEBI | | Inositol | ChEBI | | Ins | ChEBI | | L-Myo-inositol | ChEBI | | Meat sugar | ChEBI | | Meso-inositol | ChEBI | | Myoinositol | ChEBI | | Inosital | Kegg | | Iso-inositol | HMDB | | MI | HMDB | | Myoinosite | HMDB | | Phaseomannite | HMDB | | Rat antispectacled eye factor | HMDB | | Myo inositol | HMDB | | Vitamin b8 | HMDB | | Myo-inositol | HMDB |
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| Chemical Formula | C6H12O6 |
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| Average Molecular Weight | 180.1559 |
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| Monoisotopic Molecular Weight | 180.063388116 |
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| IUPAC Name | (1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol |
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| Traditional Name | L-inositol |
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| CAS Registry Number | 87-89-8 |
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| SMILES | O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O |
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| 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- |
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| InChI Key | CDAISMWEOUEBRE-GPIVLXJGSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Alcohols and polyols |
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| Direct Parent | Cyclohexanols |
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| Alternative Parents | |
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| Substituents | - Cyclohexanol
- Sugar alcohol
- Cyclitol or derivatives
- Cyclic alcohol
- Polyol
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Basal Ganglia
- Blood
- Brain
- Fibroblasts
- Intestine
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Neuron
- Placenta
- Prostate Tissue
- Semen
- Semimembranosus Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Basal Ganglia | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 45 +/- 11 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 1177 +/- 221 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 504 +/- 133 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 588.379 +/- 55.507 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 227.581 +/- 55.507 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 222.0299 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 116.566 +/- 15.542 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 183.175 (122.116-205.378) uM | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 593 +/- 126 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 7193 +/- 1232 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details |
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| External Links |
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| HMDB ID | HMDB0000211 |
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| DrugBank ID | DB13178 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB010547 |
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| KNApSAcK ID | C00001164 |
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| Chemspider ID | 10239179 |
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| KEGG Compound ID | C00137 |
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| BioCyc ID | MYO-INOSITOL |
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| BiGG ID | 33990 |
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| Wikipedia Link | Inositol |
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| METLIN ID | 5221 |
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| PubChem Compound | Not Available |
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| PDB ID | Not Available |
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| ChEBI ID | 17268 |
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| References |
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| Synthesis Reference | Iselin, Beat M. Synthesis of inositol-5-monophosphoric acid and scyllitol monophosphoric acid. Journal of the American Chemical Society (1949), 71 3822-5. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- 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.
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