Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:11 UTC |
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Update date | 2020-09-17 15:30:59 UTC |
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Primary ID | FDB010547 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Myo-Inositol |
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Description | Myo-Inositol 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 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. 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 myo-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). |
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CAS Number | 87-89-8 |
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Structure | |
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Synonyms | Synonym | 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 | (1a,2a,3a,4b,5a,6b)-Cyclohexanehexol | db_source | 1,2,3,5/4,6-Inositol | db_source | 1D-myo-Inositol | ChEBI | 1L-myo-Inositol | ChEBI | D-myo-Inositol | ChEBI | i-Inositol | db_source | L-myo-Inositol | ChEBI | meso-Inositol | db_source | Nucitol | db_source |
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Predicted Properties | |
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Chemical Formula | C6H12O6 |
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IUPAC name | (1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol |
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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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Isomeric SMILES | O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O |
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Average Molecular Weight | 180.1559 |
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Monoisotopic Molecular Weight | 180.063388116 |
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Classification |
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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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 40.00%; H 6.71%; O 53.28% | DFC |
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Melting Point | Mp 225° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 143 mg/mL at 19 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | 0 | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Myo-Inositol, 6 TMS, GC-MS Spectrum | splash10-014j-0953000000-1571a0577293e96091b1 | Spectrum | GC-MS | Myo-Inositol, 6 TMS, GC-MS Spectrum | splash10-00kb-0932000000-96ddc21293431d746ad2 | Spectrum | GC-MS | Myo-Inositol, non-derivatized, GC-MS Spectrum | splash10-00kb-0942000000-b78076224adf13bade25 | Spectrum | GC-MS | Myo-Inositol, non-derivatized, GC-MS Spectrum | splash10-00kb-0942000000-42c4e40d04b4f306535d | Spectrum | GC-MS | Myo-Inositol, 6 TMS, GC-MS Spectrum | splash10-00di-8942000000-f5d7abd38d6ff547a0a9 | Spectrum | GC-MS | Myo-Inositol, 6 TMS, GC-MS Spectrum | splash10-066r-0975000000-df7304c12b6c9bdb0f76 | Spectrum | GC-MS | Myo-Inositol, non-derivatized, GC-MS Spectrum | splash10-014j-0953000000-1571a0577293e96091b1 | Spectrum | GC-MS | Myo-Inositol, non-derivatized, GC-MS Spectrum | splash10-00kb-0932000000-96ddc21293431d746ad2 | Spectrum | GC-MS | Myo-Inositol, non-derivatized, GC-MS Spectrum | splash10-00kb-0942000000-b78076224adf13bade25 | Spectrum | GC-MS | Myo-Inositol, non-derivatized, GC-MS Spectrum | splash10-00di-8942000000-f5d7abd38d6ff547a0a9 | Spectrum | GC-MS | Myo-Inositol, non-derivatized, GC-MS Spectrum | splash10-066r-0975000000-df7304c12b6c9bdb0f76 | Spectrum | Predicted GC-MS | Myo-Inositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03dr-9700000000-18a13ab4150e6ebb20cd | Spectrum | Predicted GC-MS | Myo-Inositol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00fr-9001040000-00e67b437c4329aee95d | Spectrum | Predicted GC-MS | Myo-Inositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myo-Inositol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-0a59-3900000000-96084971c3e13a1e7451 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-001i-9000000000-1de17d7f53ca727e6d72 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-0zh9-9000000000-bef910214341056a78aa | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-004i-0900000000-41a49af846b1636763b5 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-004i-0900000000-06f9ecfccf30d40ef204 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-004i-0900000000-bca88f6782a8ed386223 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, negative | splash10-004i-1900000000-500ab195d69568b8678b | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-01ti-5900000000-a1657b54c985e2be1d19 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, negative | splash10-000i-9600000000-325cbb8dbfdeafb2b31f | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, negative | splash10-000i-9200000000-9145a4766351204e723a | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 9V, negative | splash10-000i-9100000000-2bbbcfa4733b749ec768 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 10V, negative | splash10-000i-9000000000-de0ec8731a152b612bb9 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 12V, negative | splash10-0079-9000000000-41d049d1feef94e190d4 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 14V, negative | splash10-059i-9000000000-796e728daf28d5122dee | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 15V, negative | splash10-059i-9000000000-8643e206319f3008a8d4 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 18V, negative | splash10-0abi-9000000000-98e61f19bc2842f2e97b | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 20V, negative | splash10-0ab9-9000000000-29aa062fc4d5341167b6 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-03di-1900000000-5a2897fd032a959918b3 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-000i-9000000000-71c4786b7034d5a0a0a9 | 2020-07-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-5cb39f92646251665ebf | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-2aeb7708f31c772e2d95 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08gi-8900000000-74f89711a1c6891808a4 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-8b68ff47f846a8ca1ddd | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-1900000000-03ef8572289795275d9c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0570-9300000000-950a37bd331028801e9f | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 10239179 |
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ChEMBL ID | CHEMBL1222251 |
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KEGG Compound ID | C00137 |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17268 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00211 |
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CRC / DFC (Dictionary of Food Compounds) ID | FCS22-I:FCS22-I |
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EAFUS ID | 1795 |
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Dr. Duke ID | MYO-INOSITOL|INOSITOL|MESO-INOSITOL |
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BIGG ID | 33990 |
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KNApSAcK ID | C00001164 |
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HET ID | INS |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Inositol |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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Alpha-galactosidase A | GLA | P06280 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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