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Record Information
Version3.6
Creation Date2007-04-12 22:33:06 UTC
Update Date2016-02-11 01:07:22 UTC
HMDB IDHMDB06088
Secondary Accession Numbers
  • HMDB00160
Metabolite Identification
Common NameScyllitol
DescriptionScyllitol is an isomer of cyclohexanehexol or inositol. It was first isolated from the kidneys of fish in 1858 by Staedeler and Freierchs. Scyllitol is a naturally occurring plant sugar alcohol found most abundantly in the coconut palm. It appears to accumulate in a number of human tissues and biofluids through dietary consumption. It has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379). Results reported by Viola et al (PMID: 15340856 ) suggest that high CSF concentrations of scyllo-inositol can be induced by chronic alcoholism. scyllo-Inositol (also called "scyllitol") when fed to transgenic mice that exhibit a memory disease very similar to human Alzheimer's disease, can block the accumulation of soluble amyloid-beta (Aβ) plaques in the brain. Scyllitol was found to reverse memory deficits in the mice, reduce the amount of Aβ plaque in the brains of the mice, and reversed other symptoms associated with the presence of Aβ in the brain (PMID: 16767098 ).
Structure
Thumb
Synonyms
ValueSource
(1R,2R,3R,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexolChEBI
1,2,3,4,5/6-cyclohexanehexolChEBI
(1R,2R,3R,4R,5R,6R)-Cyclohexane-1,2,3,4,5,6-hexolHMDB
1,3,5/2,4,6-cyclohexanehexolHMDB
CocositolHMDB
Cyclohexane-1,2,3,4,5,6-hexolHMDB
QuercinitolHMDB
scyllo-InositolHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional Nameepi-inositol
CAS Registry Number488-59-5
SMILES
O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)[C@H]1O
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+
InChI KeyInChIKey=CDAISMWEOUEBRE-NIPYSYMMSA-N
Chemical 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct ParentCyclitols and derivatives
Alternative Parents
Substituents
  • Cyclitol derivative
  • Cyclohexanol
  • Sugar alcohol
  • Saccharide
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point353 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.1 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
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
Polarizability16.05 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000b-9700000000-330e2df8df8562e944f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9100000000-126dbfb7ce2da687d09fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4j-9000000000-c5c2ae010c0a31be06f3View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.026 (0.0026-0.321) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified5.0 +/- 3.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified3.6 (1.9-6.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.2 (2.2-8.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.034 (0.0038-0.256) uMAdult (>18 years old)Both
Diabetes
details
BloodDetected and Quantified0.01 (0.003-0.073) uMAdult (>18 years old)Both
Diabetes
details
Cerebrospinal Fluid (CSF)Detected and Quantified72.5 +/- 55.0 uMAdult (>18 years old)Both
Alcoholism
details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Viola A, Nicoli F, Denis B, Confort-Gouny S, Le Fur Y, Ranjeva JP, Viout P, Cozzone PJ: High cerebral scyllo-inositol: a new marker of brain metabolism disturbances induced by chronic alcoholism. MAGMA. 2004 Sep;17(1):47-61. Epub 2004 Aug 31. [15340856 ]
Diabetes mellitus type 2
  1. Ostlund RE Jr, McGill JB, Herskowitz I, Kipnis DM, Santiago JV, Sherman WR: D-chiro-inositol metabolism in diabetes mellitus. Proc Natl Acad Sci U S A. 1993 Nov 1;90(21):9988-92. [8234346 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023828
KNApSAcK IDNot Available
Chemspider ID10254648
KEGG Compound IDC06153
BioCyc IDCPD-8059
BiGG IDNot Available
Wikipedia LinkScyllo-Inositol
NuGOwiki LinkHMDB06088
Metagene LinkHMDB06088
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID23927
References
Synthesis ReferenceAngyal, Stephen J.; Odier, Leon; Tate, Max E. A simple synthesis of cis-inositol. Carbohydrate Research (1995), 266(1), 143-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Viola A, Nicoli F, Denis B, Confort-Gouny S, Le Fur Y, Ranjeva JP, Viout P, Cozzone PJ: High cerebral scyllo-inositol: a new marker of brain metabolism disturbances induced by chronic alcoholism. MAGMA. 2004 Sep;17(1):47-61. Epub 2004 Aug 31. [15340856 ]
  2. McLaurin J, Kierstead ME, Brown ME, Hawkes CA, Lambermon MH, Phinney AL, Darabie AA, Cousins JE, French JE, Lan MF, Chen F, Wong SS, Mount HT, Fraser PE, Westaway D, St George-Hyslop P: Cyclohexanehexol inhibitors of Abeta aggregation prevent and reverse Alzheimer phenotype in a mouse model. Nat Med. 2006 Jul;12(7):801-8. Epub 2006 Jun 11. [16767098 ]