Inositol (PAMDB000062)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000062
Identification
Name: Inositol
Description:Inositol or cyclohexane-1,2,3,4,5,6-hexol is a chemical compound with formula C6H12O6 or (-CHOH-)6, a six-fold alcohol (polyol) of cyclohexane. It exists in nine possible stereoisomers, of which the most prominent form, widely occuring in nature, is cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol. Other naturally occurring isomers (though in minimal quantities) are scyllo-, muco-, D-chiro-, and neo-inositol. The other possible isomers are L-chiro-, allo-, epi-, and cis-inositol. (Wikipedia)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (1a,2a,3a,4b,5a,6b)1,2,3,4,5,6-Cyclohexanehexol
  • (1alpha,2alpha,3alpha,4beta,5alpha,6beta)1,2,3,4,5,6-cyclohexanehexol
  • (1r,2R,3S,4s,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol
  • (1α,2α,3α,4β,5α,6β)1,2,3,4,5,6-Cyclohexanehexol
  • 1,2,3,4,5, 6-Cyclohexanehexol
  • 1,2,3,4,5,6-Cyclohexanehexol
  • 1,2,3,4,5,6-cyclohexanehexol (ACD/Name 4.0)
  • 1,2,3,4,5,6-HEXAHYDROXY-CYCLOHEXANE
  • 1,2,3,5/4,6-Cyclohexanehexol
  • 1,2,3,5/4,6-Hexahydroxycyclohexane
  • 1D-Myo-Inositol
  • 1L-Myo-Inositol
  • meso-inositol
  • Bios i
  • Chiro-inositol
  • Cis-1,2,3,5-trans-4,6-Cyclohexanehexol
  • Cyclohexanehexol
  • Cyclohexitol
  • D-Myo-Inositol
  • Dambose
  • Hexahydroxycyclohexane
  • I-Inositol
  • Inosit
  • Inosital
  • Inosite
  • Inositene
  • Inositina
  • Inositol
  • INOSITOL (D)
  • Inositol (DCF)
  • Ins
  • Iso-Inositol
  • L-Myo-Inositol
  • M-Inositol
  • Malt extract
  • Meat sugar
  • Meso-Inositol
  • Mesoinosit
  • Mesoinosite
  • Mesoinositol
  • Mesol
  • Mesovit
  • MI
  • Mouse antialopecia factor
  • Muscle sugar
  • Myo-Inositol
  • Myoinosite
  • Myoinositol
  • Nucite
  • Phaseomannite
  • Phaseomannitol
  • Rat antispectacled eye factor
  • Scyllite
Chemical Formula: C6H12O6
Average Molecular Weight: 180.1559
Monoisotopic Molecular Weight: 180.063388116
InChI Key: CDAISMWEOUEBRE-UHFFFAOYSA-N
InChI:InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H
CAS number: 6917-35-7
IUPAC Name:cyclohexane-1,2,3,4,5,6-hexol
Traditional IUPAC Name: (-)-inositol
SMILES:OC1C(O)C(O)C(O)C(O)C1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as cyclitols and derivatives. These are compounds containing a cycloalkane moiety with one hydroxyl group on each of three or more ring atoms.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Alcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct Parent Cyclitols and derivatives
Alternative Parents
Substituents
  • Cyclitol derivative
  • Cyclohexanol
  • Sugar alcohol
  • Saccharide
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 224-227 °C
Experimental Properties:
PropertyValueSource
Water Solubility:90 mg/mLPhysProp
LogP:-4.344PhysProp
Predicted Properties
PropertyValueSource
Water Solubility485.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.77 m3·mol-1ChemAxon
Polarizability16.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
6 Water + Myo-inositol hexakisphosphate > Inositol +6 Phosphate
Sn-Glycero-3-phospho-1-inositol + Water > Glycerol 3-phosphate + Hydrogen ion + Inositol
Water + Myo-inositol 1-phosphate > Inositol + Phosphate
D-Myo-inositol 4-phosphate + Water <> Inositol + Phosphate
Water + D-Myo-inositol (1)-monophosphate > Phosphate + Inositol
myo-Inositol phosphate + Water <> Inositol + Phosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5cb39f92646251665ebfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2aeb7708f31c772e2d95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8900000000-74f89711a1c6891808a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5cb39f92646251665ebfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2aeb7708f31c772e2d95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8900000000-74f89711a1c6891808a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8b68ff47f846a8ca1dddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-03ef8572289795275d9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-9300000000-950a37bd331028801e9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8b68ff47f846a8ca1dddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-03ef8572289795275d9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-9300000000-950a37bd331028801e9fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-9000000000-0b872b8bab41938e669fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID17268
HMDB IDHMDB13777
Pubchem Compound ID892
Kegg IDC00137
ChemSpider ID868
WikipediaInositol
BioCyc IDMYO-INOSITOL
EcoCyc IDMYO-INOSITOL

Enzymes

Protein Details
• Glycerophosphoryl diester phosphodiesterase
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Locus Tag:
PA0347
Molecular weight:
42 kDa
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
Protein Details
• Inositol-1-monophosphatase
General function:
Involved in phosphatidylinositol phosphorylation
Specific function:
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate
Gene Name:
suhB
Locus Tag:
PA3818
Molecular weight:
29.5 kDa
Reactions
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate.

Transporters