Livestock Metabolome Database: Showing metabocard for Scyllitol (LMDB00469)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:50:32 UTC

Update Date

2016-09-23 18:45:34 UTC

Lmdb

LMDB00469

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Scyllitol

Description

Scyllitol 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 animal 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 animal 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,2R,3R,4R,5R,6R)-Cyclohexane-1,2,3,4,5,6-hexol	ChEBI
1,3,5/2,4,6-cyclohexanehexol	ChEBI
Cocositol	ChEBI
Quercinitol	ChEBI
Scyllitol	ChEBI
Scyllo-cyclohexanehexol	HMDB
scyllo-Inositol	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

(1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexol

Traditional Name

scyllo-inositol

CAS Registry Number

488-59-5

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 Key

CDAISMWEOUEBRE-NIPYSYMMSA-N

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

Alternative Parents

Substituents

Cyclohexanol
Sugar alcohol
Cyclitol or derivatives
Cyclic alcohol
Polyol
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

inositol (CHEBI:10642 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.6	ALOGPS
logP	-3.8	ChemAxon
logS	0.43	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.77 m³·mol⁻¹	ChemAxon
Polarizability	16.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dr-9700000000-18a13ab4150e6ebb20cd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000b-9700000000-330e2df8df8562e944f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9100000000-126dbfb7ce2da687d09f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4j-9000000000-c5c2ae010c0a31be06f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-5cb39f92646251665ebf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-2aeb7708f31c772e2d95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08gi-8900000000-74f89711a1c6891808a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8b68ff47f846a8ca1ddd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1900000000-03ef8572289795275d9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0570-9300000000-950a37bd331028801e9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-c98742ed2c27fed8805b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0570-9700000000-4e8df481dc1f1c124743	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-ea5996664694b27554a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-a3b1806f4d2d4bc9e470	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-9500000000-40e1f34ad1ad2b894cd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-5d72027b1e4acffd4c29	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Brain
Cerebrospinal Fluid (CSF)
Jejunum
Kidney
Lung
Plasma
Serum
Urine
Vitreous Humour

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Brain	Detected but not Quantified	Not Applicable	Not Available	Ovine	25959287	details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Applicable	Not Available	Ovine	17510975	details
Jejunum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Kidney	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Lung	Detected and Quantified	1.14+/-0.09 umol/g	Not Available	Porcine	23412987	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Serum	Detected and Quantified	0.00455 +/- 0.000566 uM	Not Available	Porcine	19847666	details
Serum	Detected and Quantified	0.00334 +/- 0.000455 uM	Not Available	Porcine	19847666	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Vitreous Humour	Detected but not Quantified	Not Applicable	Not Available	Caprine	24845217	details

External Links

DrugBank ID

DB03106

HMDB ID

HMDB0006088

FooDB ID

FDB023828

Phenol Explorer ID

Not Available

KNApSAcK ID

C00052408

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Not Available

Kegg Compound ID

C06153

YMDB ID

Not Available

ECMDB ID

M2MDB005347

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]

Showing metabocard for Scyllitol (LMDB00469)

Structure for LMDB00469 (Scyllitol)