Np mrd loader

Showing NP-Card for Guaiacol (NP0000376)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:40:14 UTC
NP-MRD IDNP0000376
Secondary Accession NumbersNone
Natural Product Identification
Common NameGuaiacol
DescriptionGuaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serves as a reducing co-substrate for COX reactions. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is a yellowish aromatic oil that is now commonly derived from guaiacum or wood creosote. It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation, and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation. Guaiacol is also used in the preparation of synthetic vanillin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma. (PMID 4344880 , 16152729 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000376 (Guaiacol)


  Mrv1652309272007312D          

  9  9  0  0  0  0            999 V2000
    6.7181   -6.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -5.3890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -6.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -7.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4476   -6.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000376 (Guaiacol)

HMDB0001398
     RDKit          3D
Guaiacol
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.3932    0.9830   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638   -0.1930   -0.0709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3784   -0.1498    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.9388   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678    0.9600   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3817   -0.1835    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6698   -1.3102    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -1.2781    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -2.3974    0.8321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    1.7597    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403    1.3398   -1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4584    0.7099   -0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    1.8265   -0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255    1.8596   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4644   -0.2152    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1388   -2.2136    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4415   -2.4365    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0000376 (Guaiacol)


  Mrv1652309272007312D          

  9  9  0  0  0  0            999 V2000
    6.7181   -6.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -5.3890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -6.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -7.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4476   -6.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

> <INCHI_KEY>
LHGVFZTZFXWLCP-UHFFFAOYSA-N

> <FORMULA>
C7H8O2

> <MOLECULAR_WEIGHT>
124.139

> <EXACT_MASS>
124.052429498

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.686283084612246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxyphenol

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
1.5120092286666669

> <ALOGPS_LOGS>
-0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.977540753803286

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8904950754181264

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
34.5021

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.74e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guaiacol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000376 (Guaiacol)

HMDB0001398
     RDKit          3D
Guaiacol
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.3932    0.9830   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638   -0.1930   -0.0709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3784   -0.1498    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.9388   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678    0.9600   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3817   -0.1835    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6698   -1.3102    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -1.2781    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -2.3974    0.8321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    1.7597    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403    1.3398   -1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4584    0.7099   -0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    1.8265   -0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255    1.8596   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4644   -0.2152    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1388   -2.2136    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4415   -2.4365    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
M  END
Download

PDB for NP0000376 (Guaiacol)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0      12.540 -11.618   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.895 -10.059   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.218 -12.398   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.895 -11.618   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.218 -13.956   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.567 -12.398   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.895 -14.736   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.567 -13.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.902 -12.406   0.000  0.00  0.00           C+0
CONECT    1    3    9                                                       
CONECT    2    4                                                            
CONECT    3    1    4    5                                                  
CONECT    4    2    3    6                                                  
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for NP0000376 (Guaiacol)

COMPND    HMDB0001398
HETATM    1  C1  UNL     1      -2.393   0.983  -0.547  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.764  -0.193  -0.071  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.378  -0.150   0.026  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.381   0.939  -0.306  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.768   0.960  -0.201  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.382  -0.183   0.262  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.670  -1.310   0.611  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.298  -1.278   0.488  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.445  -2.397   0.832  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.483   1.760   0.238  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.940   1.340  -1.480  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.458   0.710  -0.809  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.123   1.826  -0.667  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.326   1.860  -0.480  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.464  -0.215   0.361  1.00  0.00           H  
HETATM   16  H7  UNL     1       2.139  -2.214   0.975  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.442  -2.437   0.765  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   13
CONECT    5    6    6   14
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9
CONECT    9   17
END
Download

SMILES for NP0000376 (Guaiacol)

COC1=C(O)C=CC=C1
Download

INCHI for NP0000376 (Guaiacol)

InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
Download
View in JSmol
Synonyms
ValueSource
1-Hydroxy-2-methoxybenzeneChEBI
2-HydroxyanisoleChEBI
Catechol monomethyl etherChEBI
O-MethoxyphenolChEBI
CreodonKegg
2-MethoxyphenolHMDB
2-Methoxy-phenolHMDB
AnastilHMDB
Guaiacol (liquid) extra pureHMDB
GuaiastilHMDB
GuaicolHMDB
GuaicolinaHMDB
GuajakolHMDB
GuajolHMDB
GuasolHMDB
GuiacolHMDB
MethoxyphenolHMDB
MethylcatacholHMDB
MethylcatecholHMDB
O-GuaiacolHMDB
O-HydroxyanisoleHMDB
O-Methoxy-phenolHMDB
O-Methyl catecholHMDB
Pyrocatechol monomethyl etherHMDB
Pyroguaiac acidHMDB
2-Hydroxy-anisoleHMDB
Catechol, methylHMDB
Methyl catecholHMDB
2-Methoxyl-4-vinylphenolHMDB
GuaiacolHMDB
Chemical FormulaC7H8O2
Average Mass124.1390 Da
Monoisotopic Mass124.05243 Da
IUPAC Name2-methoxyphenol
Traditional Nameguaiacol
CAS Registry Number90-05-1
SMILES
COC1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
InChI KeyLHGVFZTZFXWLCP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agathosma betulinaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Angelica gigasLOTUS Database
Anser anserFooDB
Apium graveolensKNApSAcK Database
Apium graveolens var. dulceFooDB
    • Harvey J. Gold, Charles W. Wilson III The Volatile Flavor Substances of Celery. Journal of Food S...
Aspalathus linearisLOTUS Database
Asparagus officinalisFooDB
Astragalus pycnocephalusLOTUS Database
Azadirachta indicaLOTUS Database
Betula sp.KNApSAcK Database
Bison bisonFooDB
Blepharocalyx salicifoliusLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica hirtaKNApSAcK Database
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Castanopsis cuspidataLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Cinnamomum aromaticumFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.FooDB
Coffea canephoraKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Curcuma longaFooDB
Daphne odoraLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Ficus caricaFooDB
Gallus gallusFooDB
Geum heterocarpumLOTUS Database
Glycyrrhiza glabraLOTUS Database
Gossypium hirsutumLOTUS Database
Guaiacum officinaleKNApSAcK Database
Illicium fargesiiKNApSAcK Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melia azadirachKNApSAcK Database
Mentha x piperitaFooDB
Micromeria julianaLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Osmorhiza aristataLOTUS Database
Ovis ariesFooDB
Oxalis pes-capraeLOTUS Database
Paeonia lactifloraLOTUS Database
Paeonia suffruticosaLOTUS Database
Panax ginsengLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Photinia melanocarpaLOTUS Database
Physarum polycephalumLOTUS Database
Pimpinella anisumLOTUS Database
Prunus dulcisLOTUS Database
Scutellaria baicalensisLOTUS Database
Sesamum indicumFooDB
Silene latifoliaPlant
Sinapis albaFooDB
Solanum lycopersicum var. lycopersicumFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Thalia multifloraLOTUS Database
Verbascum lychnitisLOTUS Database
Vitex agnus-castusLOTUS Database
Vitis viniferaLOTUS Database
Zea mays L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28 °CNot Available
Boiling Point205.00 to 206.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility18.7 mg/mL at 15 °CNot Available
LogP1.32Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility67.4 g/LALOGPS
logP1.32ALOGPS
logP1.51ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)9.98ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.5 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001398
DrugBank IDDB11359
Phenol Explorer Compound ID650
FoodDB IDFDB009011
KNApSAcK IDC00002654
Chemspider ID447
KEGG Compound IDC15572
BioCyc IDCPD-400
BiGG IDNot Available
Wikipedia LinkGuaiacol
METLIN ID6217
PubChem Compound460
PDB IDNot Available
ChEBI ID28591
Good Scents IDrw1032271
References
General References
  1. Tsibris JC, Virgin SD, Khan-Dawood FS, Langenberg PW, Thomason JL, Spellacy WN: Cervicovaginal peroxidases: markers of the fertile period. Obstet Gynecol. 1986 Mar;67(3):316-20. [PubMed:3003635 ]
  2. Bieniek G, Kurkiewicz S, Wilczok T, Klimek K, Swiatkowska L, Lusiak A: occupational exposure to aromatic hydrocarbons at a coke plant: Part II. Exposure assessment of volatile organic compounds. J Occup Health. 2004 May;46(3):181-6. [PubMed:15215658 ]
  3. Ogata N, Shibata T: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73. [PubMed:11334365 ]
  4. Mutlib AE, Klein JT: Application of liquid chromatography/mass spectrometry in accelerating the identification of human liver cytochrome P450 isoforms involved in the metabolism of iloperidone. J Pharmacol Exp Ther. 1998 Sep;286(3):1285-93. [PubMed:9732390 ]
  5. Rogers LE, Lyon GM Jr, Porter FS: Spot test for vanillylmandelic acid and other guaiacols in urine of patients with neuroblastoma. Am J Clin Pathol. 1972 Oct;58(4):383-7. [PubMed:4344880 ]
  6. Pruitt KM, Kamau DN, Miller K, Mansson-Rahemtulla B, Rahemtulla F: Quantitative, standardized assays for determining the concentrations of bovine lactoperoxidase, human salivary peroxidase, and human myeloperoxidase. Anal Biochem. 1990 Dec;191(2):278-86. [PubMed:1964765 ]
  7. Kupfer A, Lawson J, Branch RA: Stereoselectivity of the arene epoxide pathway of mephenytoin hydroxylation in man. Epilepsia. 1984 Feb;25(1):1-7. [PubMed:6420144 ]
  8. Mimurai T, Yazaki K, Sawaki K, Ozawa T, Kawaguchi M: Hydroxyl radical scavenging effects of guaiacol used in traditional dental pulp sedation: reaction kinetic study. Biomed Res. 2005 Aug;26(4):139-45. [PubMed:16152729 ]