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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-13 02:06:56 UTC
HMDB IDHMDB00020
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-Hydroxyphenylacetic acid
Descriptionp-Hydroxyphenylacetic acid is an oxidative deaminated metabolite of p-tyramine. Also a metabolite of tyrosine via enteric bacteria. The bacterial origin of this compound was confirmed by the finding that this compound in urine decreased significantly after the use of the antibiotic neomycin.
Structure
Thumb
Synonyms
ValueSource
(P-Hydroxyphenyl)acetic acidChEBI
4-CarboxymethylphenolChEBI
4-Hydroxybenzeneacetic acidChEBI
4-HydroxyphenylacetateChEBI
P-Hydroxyphenylacetic acidChEBI
(P-Hydroxyphenyl)acetateGenerator
4-HydroxybenzeneacetateGenerator
P-HydroxyphenylacetateGenerator
(4-Hydroxy-phenyl)-acetateHMDB
(4-Hydroxy-phenyl)-acetic acidHMDB
(4-Hydroxy-phenyl)-essigsaeureHMDB
(4-Hydroxyphenyl)acetateHMDB
(4-Hydroxyphenyl)acetic acidHMDB
(P-Hydroxyphenyl)-acetateHMDB
(P-Hydroxyphenyl)-acetic acidHMDB
4-Hydroxy-benzeneacetateHMDB
4-Hydroxy-benzeneacetic acidHMDB
4-Hydroxyphenyl-acetic acidHMDB
Parahydroxy phenylacetateHMDB
Parahydroxy phenylacetic acidHMDB
ParahydroxyphenylacetateHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(4-hydroxyphenyl)acetic acid
Traditional Name4-hydroxyphenylacetic acid
CAS Registry Number156-38-7
SMILES
OC(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyInChIKey=XQXPVVBIMDBYFF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility60.7 mg/mLNot Available
LogP0.75HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility7.12 mg/mLALOGPS
logP0.93ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m3·mol-1ChemAxon
Polarizability14.83 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01ta-1930000000-57c9e8ddaa10569055aaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0h01-0940000000-a14203384331e709252fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-03fs-1930000000-80c21819072fb01958dcView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9410000000-678591f03aba45c2a6aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0h0r-2940000000-760b6c506072a61059c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-0900000000-e3dfb4b180d858b3a854View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-056r-9400000000-9a6cb39e019a0b40a666View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0kdl-9400000000-35ecc22161defddc7b21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0a4i-2900000000-3939c62b0d7f649ff402View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0a4i-6900000000-fdb73325a31c758496e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-4900000000-88da569804a98e1a99eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-0a95379b7cea57386b0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Bladder
  • Epidermis
  • Kidney
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
AlkaptonuriaSMP00169Not Available
Disulfiram PathwaySMP00429Not Available
Dopamine beta-hydroxylase deficiencySMP00498Not Available
HawkinsinuriaSMP00190Not Available
Monoamine oxidase-a deficiency (MAO-A)SMP00533Not Available
Tyrosine MetabolismSMP00006map00350
Tyrosinemia Type ISMP00218Not Available
Tyrosinemia, transient, of the newbornSMP00494Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.346 +/- 0.518 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified6.695 +/- 0.555 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified6.387 +/- 0.586 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified7.911 +/- 1 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified6.5 +/- 0.432 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified6.661 +/- 0.692 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified5.791 +/- 0.609 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified42.412 +/- 35.919 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.230 (0.070-0.390) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.05 +/- 0.007 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified23.530 +/- 21.821 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified26.882 +/- 32.797 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified31.0226 +/- 50.0830 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified63.228 +/- 88.730 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified21.821 +/- 8.939 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified57.181 +/- 44.0363 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected and Quantified8.18 +/- 11.0 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified7.0 (2.0-10.0) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified2.70 +/- 4.48 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified25.11 +/- 14.59 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified6.0 (2.4-9.7) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified25.268 +/- 17.653 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified5.5 (1.4-14.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified17.772 +/- 12.817 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified9.68 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 573
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 573
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 573
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 573
  • Not Applicable
details
UrineDetected and Quantified917.00 +/- 341.8 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified11 (3.5-22) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified7.0 (2.8-11.0) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified24.2 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified36.7 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified20.3 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified31.4 umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified15.3 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified24.2 (8.6-73.2) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified7.4 +/- 4.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified36.7 (8.4-142.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified20.3 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified31.4 (9.7-187.4) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified15.3 (3.2-180.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified<109.33 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified12.024 +/- 1.428 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Female
Breast cancer
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.31 +/- 0.0.03 uMAdult (>18 years old)Not SpecifiedSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.038 +/- 0.005 uMAdult (>18 years old)Not SpecifiedEpilepsy details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableAdult (>18 years old)Female
Breast cancer
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Female
Breast cancer
details
UrineDetected and Quantified30.103 +/- 31.073 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified34.998 +/- 55.908 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified18.772 +/- 21.602 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected and Quantified428.00 +/- 164.00 umol/mmol creatinineInfant (0-1 year old)BothPreterm infants details
UrineDetected and Quantified25.0 (7.0-50.5) umol/mmol creatinineAdult (>18 years old)BothMeningomyelocoele details
UrineDetected and Quantified16.0 +/- 15.0 umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Female
Breast cancer
details
Associated Disorders and Diseases
Disease References
Epilepsy
  1. Kobayashi K, Koide Y, Yoshino K, Shohmori T: [P-hydroxyphenylacetic acid concentrations in cerebrospinal fluid] No To Shinkei. 1982 Aug;34(8):769-74. [7126379 ]
Schizophrenia
  1. Kobayashi K, Koide Y, Yoshino K, Shohmori T: [P-hydroxyphenylacetic acid concentrations in cerebrospinal fluid] No To Shinkei. 1982 Aug;34(8):769-74. [7126379 ]
Lung Cancer
  1. 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. 2008 Oct 25. [18953024 ]
Spina Bifida
  1. McKibbin B, O'Gorman L, Duckworth T: Catecholamine metabolite excretion in spina bifida. J Clin Pathol. 1969 Nov;22(6):687-9. [4903899 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID573
Phenol Explorer Metabolite ID573
FoodDB IDFDB010534
KNApSAcK IDNot Available
Chemspider ID124
KEGG Compound IDC00642
BioCyc ID4-HYDROXYPHENYLACETATE
BiGG ID35599
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00020
Metagene LinkHMDB00020
METLIN ID130
PubChem Compound127
PDB ID4HP
ChEBI ID18101
References
Synthesis ReferenceQiao, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [19212411 ]
  2. 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. [15853358 ]
  3. 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. [11997029 ]
  4. 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. [7116636 ]
  5. 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. [6883916 ]
  6. 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. [6181210 ]
  7. 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. [14708889 ]
  8. 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. [455649 ]
  9. 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. [8087979 ]
  10. McKibbin B, O'Gorman L, Duckworth T: Catecholamine metabolite excretion in spina bifida. J Clin Pathol. 1969 Nov;22(6):687-9. [4903899 ]
  11. 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. [12797864 ]
  12. 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. [12971945 ]
  13. 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. [11152462 ]
  14. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [6085021 ]
  15. 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. [15721987 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
4-Hydroxyphenylacetaldehyde + NAD + Water → p-Hydroxyphenylacetic acid + NADH + Hydrogen Iondetails
4-Hydroxyphenylacetaldehyde + NADP + Water → p-Hydroxyphenylacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
4-Hydroxyphenylacetaldehyde + NAD + Water → p-Hydroxyphenylacetic acid + NADH + Hydrogen Iondetails
4-Hydroxyphenylacetaldehyde + NADP + Water → p-Hydroxyphenylacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
4-Hydroxyphenylacetaldehyde + NAD + Water → p-Hydroxyphenylacetic acid + NADH + Hydrogen Iondetails
4-Hydroxyphenylacetaldehyde + NADP + Water → p-Hydroxyphenylacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
4-Hydroxyphenylacetaldehyde + NAD + Water → p-Hydroxyphenylacetic acid + NADH + Hydrogen Iondetails
4-Hydroxyphenylacetaldehyde + NADP + Water → p-Hydroxyphenylacetic acid + NADPH + Hydrogen Iondetails