Record Information
Version2.0
Creation Date2012-05-31 10:22:20 -0600
Update Date2015-06-03 15:53:20 -0600
Secondary Accession Numbers
  • ECMDB00160
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
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
Weight:Average: 180.1559
Monoisotopic: 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
DescriptionThis compound belongs to the class of chemical entities known as cyclohexanols. These are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Sugar alcohol
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Polyol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic 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:
SMPDB Pathways:
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
6± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
7± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
7± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
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 IDNot Available
Kegg IDC00137
ChemSpider ID868
WikipediaInositol
BioCyc IDMYO-INOSITOL
EcoCyc IDMYO-INOSITOL

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing alpha-D- galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids
Gene Name:
melA
Uniprot ID:
P06720
Molecular weight:
50657
Reactions
Hydrolysis of terminal, non-reducing alpha-D-galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids.
General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
appA
Uniprot ID:
P07102
Molecular weight:
47056
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
Myo-inositol hexakisphosphate + H(2)O = 1D-myo-inositol 1,2,3,5,6-pentakisphosphate + phosphate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Uniprot ID:
P09394
Molecular weight:
40843
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in phosphatidylinositol phosphorylation
Specific function:
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate
Gene Name:
suhB
Uniprot ID:
P0ADG4
Molecular weight:
29172
Reactions
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
ugpQ
Uniprot ID:
P10908
Molecular weight:
27409
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
Specific function unknown
Gene Name:
yidK
Uniprot ID:
P31448
Molecular weight:
62084
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368