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Showing metabocard for scyllo-Inositol (HMDB0006088)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 22:33:06 UTC
Update Date2023-02-21 17:17:14 UTC
HMDB IDHMDB0006088
Secondary Accession Numbers
  • HMDB0000160
  • HMDB00160
  • HMDB06088
Metabolite Identification
Common Namescyllo-Inositol
Descriptionscyllo-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
Data?1676999834
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006088 (scyllo-Inositol)


  Mrv1652311071917592D          

 12 12  0  0  0  0            999 V2000
   -1.4275    0.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4261    0.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271   -0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157    0.4132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7158   -0.4118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0011   -0.8244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7133   -0.4118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7134    0.4132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0012    0.8258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0011    1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6  1  1  1  0  0  0
  7  2  1  6  0  0  0
  8  5  1  1  0  0  0
  9  4  1  6  0  0  0
 10  3  1  1  0  0  0
 11 12  1  6  0  0  0
M  END
Download

3D MOL for HMDB0006088 (scyllo-Inositol)

HMDB0006088
     RDKit          3D
scyllo-Inositol
 24 24  0  0  0  0  0  0  0  0999 V2000
   -1.9639    0.9130   -1.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0201    1.1087   -0.0772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1081   -0.0147    0.9275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4606    0.2743    2.1136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174   -1.3239    0.3723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7010   -1.9523   -0.2346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743   -1.1957   -0.5132 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5240   -2.1721   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    0.1352   -0.4186 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2574    0.1875   -1.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482    1.2997   -0.6369 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9569    2.4502   -0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3120    1.7874   -1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    2.0372    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -0.1100    1.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731    0.3986    2.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551   -1.9658    1.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4687   -2.5044   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -1.3946   -1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -2.0089    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516    0.2541    0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670    0.0911   -0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808    1.4743   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585    2.2312    0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  2  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  1
  4 16  1  0
  5 17  1  1
  6 18  1  0
  7 19  1  6
  8 20  1  0
  9 21  1  1
 10 22  1  0
 11 23  1  6
 12 24  1  0
M  END
Download

3D SDF for HMDB0006088 (scyllo-Inositol)


  Mrv1652311071917592D          

 12 12  0  0  0  0            999 V2000
   -1.4275    0.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4261    0.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271   -0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157    0.4132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7158   -0.4118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0011   -0.8244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7133   -0.4118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7134    0.4132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0012    0.8258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0011    1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6  1  1  1  0  0  0
  7  2  1  6  0  0  0
  8  5  1  1  0  0  0
  9  4  1  6  0  0  0
 10  3  1  1  0  0  0
 11 12  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0006088

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.1559

> <EXACT_MASS>
180.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.13060151121906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.59

> <JCHEM_LOGP>
-3.782009652

> <ALOGPS_LOGS>
0.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.908097249605351

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.285497953856298

> <JCHEM_PKA_STRONGEST_BASIC>
-3.645759838065448

> <JCHEM_POLAR_SURFACE_AREA>
121.38000000000001

> <JCHEM_REFRACTIVITY>
35.775

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.85e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
scyllo-inositol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0006088 (scyllo-Inositol)

HMDB0006088
     RDKit          3D
scyllo-Inositol
 24 24  0  0  0  0  0  0  0  0999 V2000
   -1.9639    0.9130   -1.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0201    1.1087   -0.0772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1081   -0.0147    0.9275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4606    0.2743    2.1136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174   -1.3239    0.3723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7010   -1.9523   -0.2346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743   -1.1957   -0.5132 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5240   -2.1721   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    0.1352   -0.4186 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2574    0.1875   -1.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482    1.2997   -0.6369 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9569    2.4502   -0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3120    1.7874   -1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    2.0372    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -0.1100    1.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731    0.3986    2.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551   -1.9658    1.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4687   -2.5044   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -1.3946   -1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -2.0089    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516    0.2541    0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670    0.0911   -0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808    1.4743   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585    2.2312    0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  2  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  1
  4 16  1  0
  5 17  1  1
  6 18  1  0
  7 19  1  6
  8 20  1  0
  9 21  1  1
 10 22  1  0
 11 23  1  6
 12 24  1  0
M  END
Download

PDB for HMDB0006088 (scyllo-Inositol)

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
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3D PDB for HMDB0006088 (scyllo-Inositol)

COMPND    HMDB0006088
HETATM    1  O1  UNL     1      -1.964   0.913  -1.077  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.020   1.109  -0.077  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.108  -0.015   0.928  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.461   0.274   2.114  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.617  -1.324   0.372  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.701  -1.952  -0.235  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.574  -1.196  -0.513  1.00  0.00           C  
HETATM    8  O4  UNL     1       1.524  -2.172  -0.159  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.267   0.135  -0.419  1.00  0.00           C  
HETATM   10  O5  UNL     1       2.257   0.188  -1.396  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.348   1.300  -0.637  1.00  0.00           C  
HETATM   12  O6  UNL     1       0.957   2.450  -0.114  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.312   1.787  -1.403  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.333   2.037   0.466  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.202  -0.110   1.184  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.073   0.399   2.882  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.355  -1.966   1.261  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.469  -2.504  -0.999  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.341  -1.395  -1.588  1.00  0.00           H  
HETATM   20  H8  UNL     1       1.888  -2.009   0.757  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.752   0.254   0.577  1.00  0.00           H  
HETATM   22  H10 UNL     1       3.167   0.091  -0.997  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.281   1.474  -1.738  1.00  0.00           H  
HETATM   24  H12 UNL     1       1.258   2.231   0.811  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   11   14
CONECT    3    4    5   15
CONECT    4   16
CONECT    5    6    7   17
CONECT    6   18
CONECT    7    8    9   19
CONECT    8   20
CONECT    9   10   11   21
CONECT   10   22
CONECT   11   12   23
CONECT   12   24
END
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SMILES for HMDB0006088 (scyllo-Inositol)

O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
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INCHI for HMDB0006088 (scyllo-Inositol)

InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3+,4+,5-,6-
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(1R,2R,3R,4R,5R,6R)-Cyclohexane-1,2,3,4,5,6-hexolChEBI
1,3,5/2,4,6-cyclohexanehexolChEBI
CocositolChEBI
QuercinitolChEBI
ScyllitolChEBI
Scyllo-cyclohexanehexolHMDB
scyllo-InositolHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexol
Traditional Namescyllo-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 KeyCDAISMWEOUEBRE-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point353 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.1 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility485 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.78 m³·mol⁻¹ChemAxon
Polarizability16.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+144.2330932474
DeepCCS[M-H]-141.83430932474
DeepCCS[M-2H]-176.4630932474
DeepCCS[M+Na]+150.81430932474
AllCCS[M+H]+142.332859911
AllCCS[M+H-H2O]+138.132859911
AllCCS[M+NH4]+146.132859911
AllCCS[M+Na]+147.232859911
AllCCS[M-H]-129.532859911
AllCCS[M+Na-2H]-130.532859911
AllCCS[M+HCOO]-131.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.0.04 minutes32390414
Predicted by Siyang on May 30, 202210.3057 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.83 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid364.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid651.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid354.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid18.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid207.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid97.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid311.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid223.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)703.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid613.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid42.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid843.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid212.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid326.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate766.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA463.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water367.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
scyllo-InositolO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O3553.7Standard polar33892256
scyllo-InositolO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O2007.7Standard non polar33892256
scyllo-InositolO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O1920.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
scyllo-Inositol,1TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O1743.3Semi standard non polar33892256
scyllo-Inositol,2TMS,isomer #1C[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]1O1708.2Semi standard non polar33892256
scyllo-Inositol,2TMS,isomer #2C[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]1O1721.1Semi standard non polar33892256
scyllo-Inositol,2TMS,isomer #3C[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]1O1735.0Semi standard non polar33892256
scyllo-Inositol,2TMS,isomer #4C[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)C1708.2Semi standard non polar33892256
scyllo-Inositol,3TMS,isomer #1C[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)C1686.0Semi standard non polar33892256
scyllo-Inositol,3TMS,isomer #2C[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]1O1735.6Semi standard non polar33892256
scyllo-Inositol,3TMS,isomer #3C[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]1O1735.6Semi standard non polar33892256
scyllo-Inositol,3TMS,isomer #4C[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]1O1780.1Semi standard non polar33892256
scyllo-Inositol,4TMS,isomer #1C[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)C1804.7Semi standard non polar33892256
scyllo-Inositol,4TMS,isomer #2C[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]1O1858.6Semi standard non polar33892256
scyllo-Inositol,4TMS,isomer #3C[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)C1804.7Semi standard non polar33892256
scyllo-Inositol,4TMS,isomer #4C[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]1O1854.5Semi standard non polar33892256
scyllo-Inositol,5TMS,isomer #1C[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)C1934.2Semi standard non polar33892256
scyllo-Inositol,6TMS,isomer #1C[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)C2009.2Semi standard non polar33892256
scyllo-Inositol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O2020.4Semi standard non polar33892256
scyllo-Inositol,2TBDMS,isomer #1CC(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]1O2193.7Semi standard non polar33892256
scyllo-Inositol,2TBDMS,isomer #2CC(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]1O2206.2Semi standard non polar33892256
scyllo-Inositol,2TBDMS,isomer #3CC(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]1O2236.9Semi standard non polar33892256
scyllo-Inositol,2TBDMS,isomer #4CC(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)C2193.7Semi standard non polar33892256
scyllo-Inositol,3TBDMS,isomer #1CC(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)C2456.9Semi standard non polar33892256
scyllo-Inositol,3TBDMS,isomer #2CC(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]1O2490.3Semi standard non polar33892256
scyllo-Inositol,3TBDMS,isomer #3CC(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]1O2490.3Semi standard non polar33892256
scyllo-Inositol,3TBDMS,isomer #4CC(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]1O2511.9Semi standard non polar33892256
scyllo-Inositol,4TBDMS,isomer #1CC(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)C2713.4Semi standard non polar33892256
scyllo-Inositol,4TBDMS,isomer #2CC(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]1O2733.1Semi standard non polar33892256
scyllo-Inositol,4TBDMS,isomer #3CC(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)C2713.4Semi standard non polar33892256
scyllo-Inositol,4TBDMS,isomer #4CC(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]1O2735.3Semi standard non polar33892256
scyllo-Inositol,5TBDMS,isomer #1CC(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)C2931.4Semi standard non polar33892256
scyllo-Inositol,6TBDMS,isomer #1CC(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)C3172.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - scyllo-Inositol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-9700000000-18a13ab4150e6ebb20cd2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - scyllo-Inositol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - scyllo-Inositol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000b-9700000000-330e2df8df8562e944f92018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - scyllo-Inositol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0002-9100000000-126dbfb7ce2da687d09f2018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - scyllo-Inositol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4j-9000000000-c5c2ae010c0a31be06f32018-05-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 10V, Positive-QTOFsplash10-001i-0900000000-5cb39f92646251665ebf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 20V, Positive-QTOFsplash10-001i-0900000000-2aeb7708f31c772e2d952017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 40V, Positive-QTOFsplash10-08gi-8900000000-74f89711a1c6891808a42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 10V, Negative-QTOFsplash10-004i-0900000000-8b68ff47f846a8ca1ddd2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 20V, Negative-QTOFsplash10-004i-1900000000-03ef8572289795275d9c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 40V, Negative-QTOFsplash10-0570-9300000000-950a37bd331028801e9f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 10V, Negative-QTOFsplash10-004i-0900000000-c98742ed2c27fed8805b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 20V, Negative-QTOFsplash10-0570-9700000000-4e8df481dc1f1c1247432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 40V, Negative-QTOFsplash10-0a4i-9000000000-ea5996664694b27554a82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 10V, Positive-QTOFsplash10-001i-0900000000-a3b1806f4d2d4bc9e4702021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 20V, Positive-QTOFsplash10-03e9-9500000000-40e1f34ad1ad2b894cd92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - scyllo-Inositol 40V, Positive-QTOFsplash10-03dl-9000000000-5d72027b1e4acffd4c292021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 QuantifiedInfant (0-1 year old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
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. [PubMed:8234346 ]
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. [PubMed:15340856 ]
Colorectal cancer
  1. 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
DrugBank IDDB03106
Phenol Explorer Compound IDNot Available
FooDB IDFDB023828
KNApSAcK IDC00052408
Chemspider ID10254646
KEGG Compound IDC06153
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkScyllo-Inositol
METLIN IDNot Available
PubChem CompoundNot Available
PDB ID2H3
ChEBI ID10642
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000480
Good Scents IDrw1906821
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. [PubMed: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. [PubMed:16767098 ]