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Identification
YMDB IDYMDB00173
NameMyoinositol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionmyo-Inositol, 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. myo-Inositol is an extremely weak basic (essentially neutral) compound (based on its pKa). myo-Inositol exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • cis-1,2,3,5-trans-4,6-Cyclohexanehexol
  • i-Inositol
  • iso-Inositol
  • Meat sugar
  • meso-Inositol
  • MI
  • Myo-Inositol
  • Myoinosite
  • Myoinositol
  • Phaseomannite
  • Rat antispectacled eye factor
  • (1R,2R,3S,4S,5R,6S)-Cyclohexane-1,2,3,4,5,6-hexol
  • 1,2,3,4,5,6-HEXAHYDROXY-cyclohexane
  • 1,2,3,5/4,6-cyclohexanehexol
  • 1D-Myo-inositol
  • 1l-Myo-inositol
  • Bios I
  • Cyclohexitol
  • D-Myo-inositol
  • Dambose
  • Inosite
  • Inositol
  • Ins
  • L-Myo-inositol
  • Inosital
  • Myo inositol
  • Vitamin b8
CAS number87-89-8
WeightAverage: 180.1559
Monoisotopic: 180.063388116
InChI KeyCDAISMWEOUEBRE-GPIVLXJGSA-N
InChIInChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-
IUPAC Name(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional IUPAC NameL-inositol
Chemical FormulaC6H12O6
SMILES[H]O[C@@]1([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]([H])(O[H])[C@]1([H])O[H]
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point225 °C
Experimental Properties
PropertyValueReference
Water Solubility143 mg/mL at 19 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility485 g/LALOGPS
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
Refractivity35.77 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cell envelope
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Inositol MetabolismPW002498 ThumbThumb?image type=greyscaleThumb?image type=simple
Inositol phosphate metabolismPW002495 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Galactose metabolismec00052 Map00052
Inositol phosphate metabolismec00562 Map00562
SMPDB Reactions
D-Myo-inositol 4-phosphate + waterMyoinositol + phosphate
1D-myo-inositol 3-phosphate + waterMyoinositol + phosphate
1D-myo-inositol 3-phosphate + waterMyoinositol + phosphate
D-Myo-inositol 4-phosphate + waterMyoinositol + Phosphoric acid
Myoinositol + oxygen → D-Glucuronic acid + water
KEGG Reactions
1D-myo-inositol 1-phosphate + waterMyoinositol + phosphate
Myoinositol + CDP-diacylglycerol → Cytidine monophosphate + 1-Phosphatidyl-D-myo-inositol + hydron
Myoinositol + CDP-diacylglycerol ↔ Cytidine monophosphate + 1-Phosphatidyl-D-myo-inositol + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Murray, M., Greenberg, M. L. (2000). "Expression of yeast INM1 encoding inositol monophosphatase is regulated by inositol, carbon source and growth stage and is decreased by lithium and valproate." Mol Microbiol 36:651-661.10844654
  • Nikawa, J., Yamashita, S. (1997). "Phosphatidylinositol synthase from yeast." Biochim Biophys Acta 1348:173-178.9370330
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
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.
External Links:
ResourceLink
CHEBI ID17268
HMDB IDHMDB00211
Pubchem Compound ID892
Kegg IDC00137
ChemSpider ID23203338
FOODB IDFDB010547
WikipediaInositol
BioCyc IDMYO-INOSITOL

Enzymes

General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
CDP-diacylglycerol + myo-inositol = CMP + phosphatidyl-1D-myo-inositol
Gene Name:
PIS1
Uniprot ID:
P06197
Molecular weight:
24823.5
Reactions
CDP-diacylglycerol + myo-inositol → CMP + phosphatidyl-1D-myo-inositol.
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Responsible for the provision of inositol required for synthesis of phosphatidylinositol and polyphosphoinositides and involved in the inositol cycle of calcium signaling
Gene Name:
INM2
Uniprot ID:
Q05533
Molecular weight:
32092.40039
Reactions
Myo-inositol phosphate + H(2)O → myo-inositol + phosphate.
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Responsible for the provision of inositol required for synthesis of phosphatidylinositol and polyphosphoinositides
Gene Name:
INM1
Uniprot ID:
P38710
Molecular weight:
32823.0
Reactions
Myo-inositol phosphate + H(2)O → myo-inositol + phosphate.

Transporters

General function:
Involved in transmembrane transporter activity
Specific function:
Major transporter for myo-inositol
Gene Name:
ITR1
Uniprot ID:
P30605
Molecular weight:
63569.10156
General function:
Involved in DNA binding
Specific function:
Integrase (IN) targets the VLP to the nucleus, where a subparticle preintegration complex (PIC) containing at least integrase and the newly synthesized dsDNA copy of the retrotransposon must transit the nuclear membrane. Once in the nucleus, integrase performs the integration of the dsDNA into the host genome
Gene Name:
TY1B-OL
Uniprot ID:
Q12273
Molecular weight:
198613.0
Reactions
Deoxynucleoside triphosphate + DNA(n) → diphosphate + DNA(n+1).