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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 22:33:06 UTC

Update Date

2023-02-21 17:17:14 UTC

HMDB ID

HMDB0006088

Secondary Accession Numbers

HMDB0000160
HMDB00160
HMDB06088

Metabolite Identification

Common Name

scyllo-Inositol

Description

scyllo-Inositol or scyllitol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. scyllo-Inositol was first isolated from the kidneys of fish in 1858 by Staedeler and Freierchs. scyllo-Inositol 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 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. scyllo-Inositol 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 07-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-NOV-19         0                                  
HETATM    1  O   UNK     0      -2.665   1.541   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -2.666  -1.538   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       2.662   1.538   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.664  -1.535   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.002  -3.076   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.336   0.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.336  -0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.002  -1.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.331  -0.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.332   0.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.002   1.541   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.002   3.076   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   10                                                            
CONECT    4    9                                                            
CONECT    5    8                                                            
CONECT    6    7   11    1                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7    9    5                                                  
CONECT    9    8   10    4                                                  
CONECT   10    9   11    3                                                  
CONECT   11    6   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

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-CDRYSYESSA-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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8234346)
Cerebrospinal Fluid (CSF) (PMID: 15340856)
Saliva (PMID: 22308371)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 22411374)

Source

Exogenous

Exogenous (HMDB: HMDB0006088)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Ethanol Consumption (MarkerDB: MDB00000480)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	353 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.1 mg/mL at 18 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	485 g/L	ALOGPS
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	35.78 m³·mol⁻¹	ChemAxon
Polarizability	16.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	144.23	30932474
DeepCCS	[M-H]-	141.834	30932474
DeepCCS	[M-2H]-	176.46	30932474
DeepCCS	[M+Na]+	150.814	30932474
AllCCS	[M+H]+	142.3	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	129.5	32859911
AllCCS	[M+Na-2H]-	130.5	32859911
AllCCS	[M+HCOO]-	131.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
scyllo-Inositol	O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	3553.7	Standard polar	33892256
scyllo-Inositol	O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	2007.7	Standard non polar	33892256
scyllo-Inositol	O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	1920.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
scyllo-Inositol,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O	1743.3	Semi standard non polar	33892256
scyllo-Inositol,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O	1708.2	Semi standard non polar	33892256
scyllo-Inositol,2TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	1721.1	Semi standard non polar	33892256
scyllo-Inositol,2TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1735.0	Semi standard non polar	33892256
scyllo-Inositol,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1708.2	Semi standard non polar	33892256
scyllo-Inositol,3TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1686.0	Semi standard non polar	33892256
scyllo-Inositol,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	1735.6	Semi standard non polar	33892256
scyllo-Inositol,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	1735.6	Semi standard non polar	33892256
scyllo-Inositol,3TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	1780.1	Semi standard non polar	33892256
scyllo-Inositol,4TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1804.7	Semi standard non polar	33892256
scyllo-Inositol,4TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1858.6	Semi standard non polar	33892256
scyllo-Inositol,4TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1804.7	Semi standard non polar	33892256
scyllo-Inositol,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	1854.5	Semi standard non polar	33892256
scyllo-Inositol,5TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1934.2	Semi standard non polar	33892256
scyllo-Inositol,6TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2009.2	Semi standard non polar	33892256
scyllo-Inositol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O	2020.4	Semi standard non polar	33892256
scyllo-Inositol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O	2193.7	Semi standard non polar	33892256
scyllo-Inositol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2206.2	Semi standard non polar	33892256
scyllo-Inositol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2236.9	Semi standard non polar	33892256
scyllo-Inositol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2193.7	Semi standard non polar	33892256
scyllo-Inositol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2456.9	Semi standard non polar	33892256
scyllo-Inositol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2490.3	Semi standard non polar	33892256
scyllo-Inositol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2490.3	Semi standard non polar	33892256
scyllo-Inositol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2511.9	Semi standard non polar	33892256
scyllo-Inositol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2713.4	Semi standard non polar	33892256
scyllo-Inositol,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2733.1	Semi standard non polar	33892256
scyllo-Inositol,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2713.4	Semi standard non polar	33892256
scyllo-Inositol,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2735.3	Semi standard non polar	33892256
scyllo-Inositol,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2931.4	Semi standard non polar	33892256
scyllo-Inositol,6TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3172.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - scyllo-Inositol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dr-9700000000-18a13ab4150e6ebb20cd	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - scyllo-Inositol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - scyllo-Inositol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000b-9700000000-330e2df8df8562e944f9	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - scyllo-Inositol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0002-9100000000-126dbfb7ce2da687d09f	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - scyllo-Inositol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4j-9000000000-c5c2ae010c0a31be06f3	2018-05-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 10V, Positive-QTOF	splash10-001i-0900000000-5cb39f92646251665ebf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 20V, Positive-QTOF	splash10-001i-0900000000-2aeb7708f31c772e2d95	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 40V, Positive-QTOF	splash10-08gi-8900000000-74f89711a1c6891808a4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 10V, Negative-QTOF	splash10-004i-0900000000-8b68ff47f846a8ca1ddd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 20V, Negative-QTOF	splash10-004i-1900000000-03ef8572289795275d9c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 40V, Negative-QTOF	splash10-0570-9300000000-950a37bd331028801e9f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 10V, Negative-QTOF	splash10-004i-0900000000-c98742ed2c27fed8805b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 20V, Negative-QTOF	splash10-0570-9700000000-4e8df481dc1f1c124743	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 40V, Negative-QTOF	splash10-0a4i-9000000000-ea5996664694b27554a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 10V, Positive-QTOF	splash10-001i-0900000000-a3b1806f4d2d4bc9e470	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 20V, Positive-QTOF	splash10-03e9-9500000000-40e1f34ad1ad2b894cd9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - scyllo-Inositol 40V, Positive-QTOF	splash10-03dl-9000000000-5d72027b1e4acffd4c29	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.026 (0.0026-0.321) uM	Adult (>18 years old)	Both	Normal	8234346	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.0 +/- 3.0 uM	Adult (>18 years old)	Both	Normal	15340856	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	3.6 (1.9-6.9) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	4.2 (2.2-8.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.034 (0.0038-0.256) uM	Adult (>18 years old)	Both	Diabetes	8234346	details
Blood	Detected and Quantified	0.01 (0.003-0.073) uM	Adult (>18 years old)	Both	Diabetes	8234346	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	72.5 +/- 55.0 uM	Adult (>18 years old)	Both	Alcoholism	15340856	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 2
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. [PubMed:8234346 ]
Alcoholism
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. [PubMed:15340856 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

125853 (Diabetes mellitus type 2)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB03106

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Scyllo-Inositol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

2H3

ChEBI ID

10642

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000480

Good Scents ID

rw1906821

References

Synthesis Reference

Angyal, 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)

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. [PubMed: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. [PubMed:16767098 ]

Showing metabocard for scyllo-Inositol (HMDB0006088)

MOL for HMDB0006088 (scyllo-Inositol)

3D MOL for HMDB0006088 (scyllo-Inositol)

3D SDF for HMDB0006088 (scyllo-Inositol)

3D-SDF for HMDB0006088 (scyllo-Inositol)

PDB for HMDB0006088 (scyllo-Inositol)

3D PDB for HMDB0006088 (scyllo-Inositol)

SMILES for HMDB0006088 (scyllo-Inositol)

INCHI for HMDB0006088 (scyllo-Inositol)

Structure for HMDB0006088 (scyllo-Inositol)

3D Structure for HMDB0006088 (scyllo-Inositol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra