Common NameMyo-inositol
Descriptionmyo-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 exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, of which cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol is the most widely occurring form in nature. The other known inositols include scyllo-inositol, muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol and cis-inositol. myo-Inositol is found naturally in many foods (particularly in cereals with high bran content) and can be used as a sweetner as it has half the sweetness of sucrose (table sugar). myo-Inositol was once considered a member of the vitamin B complex and given the name: vitamin B8. However, because it is produced by the human body from glucose, it is not an essential nutrient, and therefore cannot be called a vitamin. myo-Inositol is a precursor molecule for a number of secondary messengers including various inositol phosphates. In addition, inositol/myo-inositol is an important component of the lipids known as phosphatidylinositol (PI) phosphatidylinositol phosphate (PIP). myo-Inositol is synthesized from glucose, via glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerised by an inositol-3-phosphate synthase enzyme to myo-inositol 1-phosphate, which is then dephosphorylated by an inositol monophosphatase enzyme to give free myo-inositol. In humans, myo-inositol is primarily synthesized in the kidneys at a rate of a few grams per day. myo-Inositol can be used in the management of preterm babies who have or are at a risk of infant respiratory distress syndrome. It is also used as a treatment for polycystic ovary syndrome (PCOS). It works by increasing insulin sensitivity, which helps to improve ovarian function and reduce hyperandrogenism. Reduced levels of myo-inositol have been found in the spinal fluid of depressed patients and levels are significantly reduced in brain samples of suicide victims.
Structure
Molecular FormulaC6H12O6
Average Mass180.15590
Monoisotopic Mass180.06339
IUPAC Name(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional NameMyo-inositol
CAS Registry Number87-89-8
SMILESO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
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-
InChI KeyCDAISMWEOUEBRE-GPIVLXJGSA-N
CHEBI IDCHEBI:17268
HMDB IDHMDB0000211
Pathways
NameSMPDB/PathBank
Inositol phosphate metabolism
Galactose Metabolism
Galactosemia
Inositol Phosphate Metabolism
Phosphatidylinositol Phosphate Metabolism
Joubert syndrome
StateNot Available
Water Solubility4.85e+02 g/l
logP-2.59
logS0.43
pKa (Strongest Acidic)12.29
pKa (Strongest Basic)-3.65
Hydrogen Acceptor Count6
Hydrogen Donor Count6
Polar Surface Area121.38 Ų
Rotatable Bond Count0
Physiological Charge0
Formal Charge0
Refractivity35.78 m³·mol⁻¹
Polarizability16.14

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