Record Information
Version1.0
Creation Date2016-07-13 19:42:20 UTC
Update Date2021-04-30 20:57:58 UTC
LmdbLMDB00099
Secondary Accession NumbersNone
Metabolite Identification
Common NameOrnithine
DescriptionOrnithine is an amino acid produced in the urea cycle by the splitting off of urea from arginine. It is a central part of the urea cycle, which allows for the disposal of excess nitrogen. L-Ornithine is also a precursor of citrulline and arginine. In order for ornithine produced in the cytosol to be converted to citrulline, it must first cross the inner mitochondrial membrane into the mitochondrial matrix where it is carbamylated by ornithine transcarbamylase. This transfer is mediated by the mitochondrial ornithine transporter (SLC25A15; AF112968; ORNT1). Mutations in the mitochondrial ornithine transporter result in hyperammonemia, hyperornithinemia, homocitrullinuria (HHH) syndrome, a disorder of the urea cycle. (PMID 16256388 ) The pathophysiology of the disease may involve diminished ornithine transport into mitochondria, resulting in ornithine accumulation in the cytoplasm and reduced ability to clear carbamoyl phosphate and ammonia loads. (OMIM 838970 ).
Structure
Thumb
Synonyms
ValueSource
(S)-2,5-DiaminopentanoateChEBI
(S)-2,5-Diaminopentanoic acidChEBI
(S)-2,5-Diaminovaleric acidChEBI
(S)-alpha,delta-Diaminovaleric acidChEBI
(S)-OrnithineChEBI
(S)-2,5-DiaminovalerateGenerator
(S)-a,delta-DiaminovalerateGenerator
(S)-a,delta-Diaminovaleric acidGenerator
(S)-alpha,delta-DiaminovalerateGenerator
(S)-Α,δ-diaminovalerateGenerator
(S)-Α,δ-diaminovaleric acidGenerator
(S)-a,Δ-diaminovalerateHMDB
(S)-a,Δ-diaminovaleric acidHMDB
(+)-S-OrnithineHMDB
(S)-a,D-DiaminovalerateHMDB
(S)-a,D-Diaminovaleric acidHMDB
5-Amino-L-norvalineHMDB
L-(-)-OrnithineHMDB
L-OrnithineHMDB
2,5-Diaminopentanoic acidHMDB
Ornithine dihydrochloride, (L)-isomerHMDB
Ornithine hydrochloride, (D)-isomerHMDB
Ornithine, (D)-isomerHMDB
Ornithine, (L)-isomerHMDB
2,5 Diaminopentanoic acidHMDB
Ornithine monoacetate, (L)-isomerHMDB
Ornithine monohydrochloride, (D)-isomerHMDB
Ornithine monohydrochloride, (DL)-isomerHMDB
Ornithine phosphate (1:1), (L)-isomerHMDB
Ornithine sulfate (1:1), (L)-isomerHMDB
Ornithine hydrochloride, (DL)-isomerHMDB
Ornithine hydrochloride, (L)-isomerHMDB
Ornithine monohydrobromide, (L)-isomerHMDB
Ornithine, (DL)-isomerHMDB
Chemical FormulaC5H12N2O2
Average Molecular Weight132.161
Monoisotopic Molecular Weight132.089877638
IUPAC Name(2S)-2,5-diaminopentanoic acid
Traditional Nameornithine
CAS Registry Number70-26-8
SMILES
NCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
InChI KeyAHLPHDHHMVZTML-BYPYZUCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.6ALOGPS
logP-3.7ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.21 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0006-1920000000-b0357b8c9888abda7d80Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-0910000000-8aaa0faabf1429b90611Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-7910000000-5fa118444ceb45204aa3Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-006x-3910000000-f6d0c6492f2cab33a392Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00dr-2900000000-77222ff2d0118d3d3b57Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0006-1910000000-53c73c4fa3665c44d3b9Spectrum
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-03di-1691000000-dc14976cfee86cc828b9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0920000000-f65f61e4a3739eabb1d1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-1920000000-b0357b8c9888abda7d80Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0910000000-8aaa0faabf1429b90611Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-7910000000-5fa118444ceb45204aa3Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-006x-3910000000-f6d0c6492f2cab33a392Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-2900000000-77222ff2d0118d3d3b57Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-1910000000-53c73c4fa3665c44d3b9Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-1691000000-dc14976cfee86cc828b9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-f59681b9f46f1b738487Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-3048477975b51ae176afSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-2900000000-8d1a2cc0a88f7d9216e1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1900000000-bc40b76e8b03ef7a08f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9000000000-50fe14c2cb68fd09e32fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9300000000-bbfdea03043e52ad8a15Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01b9-6900000000-8fe592b77d2d8e4ae704Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-462b84db532c33527580Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-9c9c28d2e40d5eadacd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-e44e06092c06bb4791afSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-9000000000-4d6ccc429f5155b24654Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-dcad699e8ed7e1b19860Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-7b130437d4e1ceea277bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-0fae230bc6b21623a4bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-9000000000-5a350a8e7c607a8b9a60Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-516054b6c2f3cd4a1d02Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0793321000-9fef988b5ce019f84642Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-a612df8df5f8ba1ff7f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-97fad20414656e2b7b93Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01di-0490000000-1b137b937beb110d2e4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-e3fc95eb909e45d8e648Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-cdd9aac89a5a71814ff3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001r-9500000000-f1cc3eccf3f5ab734222Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0159-0900000000-93ce7b142d1f82f17e95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9200000000-186f270471bdec40f804Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-ebbdf0ab6d3180cba1a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-207bcc826fb2238c2cc5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-9000000000-a2f9a950fb23a6b18857Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01c9-9700000000-0364d35bb1a7c10a09c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9100000000-9c4015733140885b4957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-b32e7180e30a835008bbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Follicular Fluid
  • Kidney
  • Liver
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Follicular FluidDetected and Quantified26 +/- 0 - 31+/-0 uMNot AvailablePorcine details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected and Quantified2-150 uMNot AvailableBovine details
PlasmaDetected and Quantified138 +/- 12-139+/-40 uMNot AvailablePorcine details
PlasmaDetected and Quantified161 +/- 22-103+/-24 uMNot AvailablePorcine details
PlasmaDetected and Quantified91 +/- 1-109+/-10 uMNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected and Quantified145.91 uMNot AvailablePorcine details
PlasmaDetected and Quantified152.84 uMNot AvailablePorcine details
PlasmaDetected and Quantified258.35 uMNot AvailablePorcine details
PlasmaDetected and Quantified260.02 uMNot AvailablePorcine details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified15.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified16.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified25.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified58.7 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified17 +/- 7 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified19 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified19 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified25 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified38 +/- 13 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
SerumDetected and Quantified98.9 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified118.2 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified120.8 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified109.0285 +/- 40.9936 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified132.1 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified163.4744 +/- 50.8165 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified57.7103 +/- 27.4327 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified124.1891 +/- 57.7523 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified127.7463 +/- 52.2776 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified145.5529 +/- 52.7213 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
SerumDetected and Quantified86.3763 +/- 28.1903 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified129.7445 +/- 64.603 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified107.59 +/- 46.75 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified204.675 uMNot AvailablePorcine details
SerumDetected and Quantified102.224 uMNot AvailablePorcine details
SerumDetected and Quantified94.279 uMNot AvailablePorcine details
SerumDetected and Quantified167.75 uMNot AvailablePorcine details
SerumDetected and Quantified141.1333 +/- 73.0125 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified116.3578 +/- 54.7035 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified150.6135 +/- 66.1951 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified69 +/- 13 uMNot AvailablePorcine details
SerumDetected and Quantified129.1594 +/- 59.8333 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified120.453 +/- 55.9965 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified98.2887 +/- 44.7248 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified69.0576 +/- 22.5862 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified124.8746 +/- 35.5282 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified125.2183 +/- 63.204 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified77.9011 +/- 29.7083 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified139.4973 +/- 57.6963 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified123.4995 +/- 62.7206 uM
Normal
Ovine
    • Goldansaz et al.,...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB00129
HMDB IDHMDB0000214
FooDB IDFDB030969
Phenol Explorer IDNot Available
KNApSAcK IDC00001384
BiGG ID37976
BioCyc IDL-ORNITHINE
METLIN ID27
PDB IDNot Available
Wikipedia LinkOrnithine
Chemspider ID6026
ChEBI ID15729
PubChem Compound ID6262
Kegg Compound IDC00077
YMDB IDYMDB00353
ECMDB IDECMDB23898
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Morizono H, Woolston JE, Colombini M, Tuchman M: The use of yeast mitochondria to study the properties of wild-type and mutant human mitochondrial ornithine transporter. Mol Genet Metab. 2005 Dec;86(4):431-40. Epub 2005 Oct 26. [16256388 ]