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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:13:57 UTC |
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HMDB ID | HMDB0000020 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | p-Hydroxyphenylacetic acid |
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Description | P-hydroxyphenylacetic acid, also known as 4-Hydroxybenzeneacetate or Parahydroxy phenylacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-hydroxy-2-unsubstituted benzenoids are phenols that a unsubstituted at the 2-position. P-hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic. P-hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate. P-hydroxyphenylacetic acid can be found throughout numerous foods such as Olives, Cocoa beans, Oats, and Mushrooms. P-hydroxyphenylacetic acid can be found throughout all human tissues; and in all biofluids. Within a cell, P-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space |
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Structure | |
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Synonyms | Value | Source |
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(P-Hydroxyphenyl)acetic acid | ChEBI | 4-Carboxymethylphenol | ChEBI | 4-Hydroxybenzeneacetic acid | ChEBI | 4-Hydroxyphenylacetate | ChEBI | (P-Hydroxyphenyl)acetate | Generator | P-Hydroxyphenylacetate | Generator | 4-Hydroxybenzeneacetate | Generator | 4-Hydroxyphenylacetic acid | Generator | (4-Hydroxy-phenyl)-acetate | HMDB | (4-Hydroxy-phenyl)-acetic acid | HMDB | (4-Hydroxy-phenyl)-essigsaeure | HMDB | (4-Hydroxyphenyl)acetate | HMDB | (4-Hydroxyphenyl)acetic acid | HMDB | (P-Hydroxyphenyl)-acetate | HMDB | (P-Hydroxyphenyl)-acetic acid | HMDB | 4-Hydroxy-benzeneacetate | HMDB | 4-Hydroxy-benzeneacetic acid | HMDB | 4-Hydroxyphenyl-acetic acid | HMDB | Parahydroxy phenylacetate | HMDB | Parahydroxy phenylacetic acid | HMDB | Parahydroxyphenylacetate | HMDB | Para-hydroxyphenylacetic acid | MeSH |
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Chemical Formula | C8H8O3 |
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Average Molecular Weight | 152.1473 |
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Monoisotopic Molecular Weight | 152.047344122 |
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IUPAC Name | 2-(4-hydroxyphenyl)acetic acid |
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Traditional Name | 4-hydroxyphenylacetic acid |
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CAS Registry Number | 156-38-7 |
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SMILES | OC(=O)CC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) |
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InChI Key | XQXPVVBIMDBYFF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | 1-hydroxy-2-unsubstituted benzenoids |
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Direct Parent | 1-hydroxy-2-unsubstituted benzenoids |
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Alternative Parents | |
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Substituents | - 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 148 - 150 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 60.7 mg/mL | Not Available | LogP | 0.75 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-01ta-1930000000-57c9e8ddaa10569055aa | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0h01-0940000000-a14203384331e709252f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-03fs-1930000000-80c21819072fb01958dc | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00di-9410000000-678591f03aba45c2a6ae | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0h0r-2940000000-760b6c506072a61059c0 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-2900000000-3939c62b0d7f649ff402 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-6900000000-fdb73325a31c758496e9 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0gyk-0980000000-ed36f36969e4d51b9a8d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-01ta-1930000000-57c9e8ddaa10569055aa | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0h01-0940000000-a14203384331e709252f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-03fs-1930000000-80c21819072fb01958dc | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9410000000-678591f03aba45c2a6ae | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0h0r-2940000000-760b6c506072a61059c0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-03fs-1931100000-50456fed0c5ef95ecb57 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-4900000000-b6f6363476ffa290862f | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-004i-5930000000-abf5245dd22d012d04f8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0pb9-0900000000-e3dfb4b180d858b3a854 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-056r-9400000000-9a6cb39e019a0b40a666 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0kdl-9400000000-35ecc22161defddc7b21 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive | splash10-0a4i-2900000000-3939c62b0d7f649ff402 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive | splash10-0a4i-6900000000-fdb73325a31c758496e9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0a4i-4900000000-88da569804a98e1a99ea | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a4i-9300000000-eef23e2f30d876f4a1f9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4i-9000000000-0a95379b7cea57386b0b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-4900000000-88da569804a98e1a99ea | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9300000000-eef23e2f30d876f4a1f9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-0a95379b7cea57386b0b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0a4i-0900000000-02cd23fa5ff37594d2be | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0a4i-0900000000-bbac468eb7ce6ea99123 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4i-1900000000-05d18e7bb4163e35e2aa | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4i-1900000000-9a0086561d6f8a169670 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udr-0900000000-398dff08b5b2a56e658c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0900000000-5f75ea6de2d6bad624d8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0zfr-0900000000-7ce02fea5a9ef38024f2 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zfr-0900000000-12e388b0927ed1c6e166 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a59-2900000000-ae1870eee4853c57a447 | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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Tissue Locations | - Bladder
- Epidermis
- Kidney
- Prostate
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 6.346 +/- 0.518 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 6.695 +/- 0.555 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 6.387 +/- 0.586 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 7.911 +/- 1 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 6.5 +/- 0.432 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 6.661 +/- 0.692 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 5.791 +/- 0.609 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 42.412 +/- 35.919 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.230 (0.070-0.390) uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.05 +/- 0.007 uM | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 23.530 +/- 21.821 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected and Quantified | 26.882 +/- 32.797 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 31.0226 +/- 50.0830 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 63.228 +/- 88.730 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Infant (0-1 year old) | Not Available | Normal | | details | Feces | Detected and Quantified | 21.821 +/- 8.939 nmol/g wet feces | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 3.714 (0.513-31.226) nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 57.181 +/- 44.0363 nmol/g wet feces | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Infant (0-1 year old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Infant (0-1 year old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 8.18 +/- 11.0 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 7.0 (2.0-10.0) uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 2.70 +/- 4.48 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 25.11 +/- 14.59 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 6.0 (2.4-9.7) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 25.268 +/- 17.653 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 5.8-12 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <185.774 umol/mmol creatinine | Infant (0-1 year old) | Male | Normal | | details | Urine | Detected and Quantified | 44.586 +/- 28.981 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 56.475 +/- 36.412 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 69.108 +/- 70.594 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 5.5 (1.4-14.6) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 17.772 +/- 12.817 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 9.68 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 573 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 573 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 573 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 573 | | details | Urine | Detected and Quantified | 917.00 +/- 341.8 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 11 (3.5-22) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 7.0 (2.8-11.0) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 24.2 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 36.7 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 20.3 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 31.4 umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 15.3 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 24.2 (8.6-73.2) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 10.455 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 7.4 +/- 4.4 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 36.7 (8.4-142.0) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 1.680-101.700 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 20.3 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 31.4 (9.7-187.4) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 15.3 (3.2-180.2) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 5.2-12 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | <109.33 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 12.024 +/- 1.428 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | | Adult (>18 years old) | Female | Breast cancer | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.31 +/- 0.0.03 uM | Adult (>18 years old) | Not Specified | Schizophrenia | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.038 +/- 0.005 uM | Adult (>18 years old) | Not Specified | Epilepsy | | details | Cerebrospinal Fluid (CSF) | Detected but not Quantified | | Adult (>18 years old) | Female | Breast cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Ulcerative colitis | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Crohn disease | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal Cancer | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Female | Breast cancer | | details | Urine | Detected and Quantified | 30.103 +/- 31.073 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 34.998 +/- 55.908 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details | Urine | Detected and Quantified | 24.522 umol/mmol creatinine | Infant (0-1 year old) | Male | Fumarase deficiency | | details | Urine | Detected and Quantified | 44.586 +/- 66.136 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 46.0719 +/- 45.329 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 47.558 +/- 69.108 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 18.772 +/- 21.602 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Hypertension (mild) | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Hypertension (mild) | | details | Urine | Detected and Quantified | 428.00 +/- 164.00 umol/mmol creatinine | Infant (0-1 year old) | Both | Preterm infants | | details | Urine | Detected and Quantified | 25.0 (7.0-50.5) umol/mmol creatinine | Adult (>18 years old) | Both | Meningomyelocoele | | details | Urine | Detected and Quantified | 16.0 +/- 15.0 umol/mmol creatinine | Not Specified | Both | Lung cancer | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Male | Cardiosvacular risk | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Female | Breast cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Schizophrenia |
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- Kobayashi K, Koide Y, Yoshino K, Shohmori T: [P-hydroxyphenylacetic acid concentrations in cerebrospinal fluid]. No To Shinkei. 1982 Aug;34(8):769-74. [PubMed:7126379 ]
| Epilepsy |
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- Kobayashi K, Koide Y, Yoshino K, Shohmori T: [P-hydroxyphenylacetic acid concentrations in cerebrospinal fluid]. No To Shinkei. 1982 Aug;34(8):769-74. [PubMed:7126379 ]
| Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- 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 ]
| Ulcerative colitis |
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- Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
| Crohn's disease |
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- Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
| Lung Cancer |
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- Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
| Spina Bifida |
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- McKibbin B, O'Gorman L, Duckworth T: Catecholamine metabolite excretion in spina bifida. J Clin Pathol. 1969 Nov;22(6):687-9. [PubMed:4903899 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
| Perillyl alcohol administration for cancer treatment |
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- Nam H, Chung BC, Kim Y, Lee K, Lee D: Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification. Bioinformatics. 2009 Dec 1;25(23):3151-7. doi: 10.1093/bioinformatics/btp558. Epub 2009 Sep 25. [PubMed:19783829 ]
| Fumarase deficiency |
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- Bastug O, Kardas F, Ozturk MA, Halis H, Memur S, Korkmaz L, Tag Z, Gunes T: A rare cause of opistotonus; fumaric aciduria: The first case presentation in Turkey. Turk Pediatri Ars. 2014 Mar 1;49(1):74-6. doi: 10.5152/tpa.2014.442. eCollection 2014 Mar. [PubMed:26078636 ]
| Phenylketonuria |
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- Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | 573 |
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FoodDB ID | FDB010534 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 124 |
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KEGG Compound ID | C00642 |
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BioCyc ID | 4-HYDROXYPHENYLACETATE |
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BiGG ID | 35599 |
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Wikipedia Link | 4-hydroxyphenylacetic_acid |
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METLIN ID | 130 |
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PubChem Compound | 127 |
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PDB ID | 4HP |
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ChEBI ID | 18101 |
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References |
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Synthesis Reference | Qiao, Xi-long; Tian, Hui; Li, Wen; Zhao, Xiu-yun; Zhang, Jin-fang. Study of 4-hydroxyphenylacetic acid synthesis from glyoxalic acid. Hebei Gongye Keji (2005), 22(5), 264-266. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Hirota S, Takahama U, Ly TN, Yamauchi R: Quercetin-dependent inhibition of nitration induced by peroxidase/H2O2/nitrite systems in human saliva and characterization of an oxidation product of quercetin formed during the inhibition. J Agric Food Chem. 2005 May 4;53(9):3265-72. [PubMed:15853358 ]
- Takahama U, Oniki T, Murata H: The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002 May 8;518(1-3):116-8. [PubMed:11997029 ]
- Kobayashi K, Koide Y, Shohmori T: Determination of p-hydroxyphenylacetic acid in cerebrospinal fluid by high-performance liquid chromatography with electrochemical detection. Clin Chim Acta. 1982 Aug 4;123(1-2):161-8. [PubMed:7116636 ]
- Tyce GM, Stockard J, Sharpless NS, Muenter MD: Excretion of amines and their metabolites by two patients in hepatic coma treated with L-dopa. Clin Pharmacol Ther. 1983 Sep;34(3):390-8. [PubMed:6883916 ]
- Young SN, Davis BA, Gauthier S: Precursors and metabolites of phenylethylamine, m and p-tyramine and tryptamine in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1982 Jul;45(7):633-9. [PubMed:6181210 ]
- Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
- Muskiet FA, Groen A: Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma. Clin Chem. 1979 Jul;25(7):1281-4. [PubMed:455649 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- McKibbin B, O'Gorman L, Duckworth T: Catecholamine metabolite excretion in spina bifida. J Clin Pathol. 1969 Nov;22(6):687-9. [PubMed:4903899 ]
- Mani AR, Pannala AS, Orie NN, Ollosson R, Harry D, Rice-Evans CA, Moore KP: Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine. Biochem J. 2003 Sep 1;374(Pt 2):521-7. [PubMed:12797864 ]
- Takahama U, Hirota S, Nishioka T, Oniki T: Human salivary peroxidase-catalyzed oxidation of nitrite and nitration of salivary components 4-hydroxyphenylacetic acid and proteins. Arch Oral Biol. 2003 Oct;48(10):679-90. [PubMed:12971945 ]
- Quijano C, Hernandez-Saavedra D, Castro L, McCord JM, Freeman BA, Radi R: Reaction of peroxynitrite with Mn-superoxide dismutase. Role of the metal center in decomposition kinetics and nitration. J Biol Chem. 2001 Apr 13;276(15):11631-8. Epub 2001 Jan 4. [PubMed:11152462 ]
- Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
- Jenner AM, Rafter J, Halliwell B: Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med. 2005 Mar 15;38(6):763-72. [PubMed:15721987 ]
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