Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:30:46 UTC
HMDB IDHMDB0000755
Secondary Accession Numbers
  • HMDB00755
Metabolite Identification
Common NameHydroxyphenyllactic acid
DescriptionHydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID: 4720815 ). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358 ). However, the D-form of hydroxyphenyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358 ). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produce considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754 ). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754 ). Hydroxyphenyllactic acid is a microbial metabolite found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416 ).
Structure
Data?1582752154
Synonyms
ValueSource
2-Hydroxy-3-(4-hydroxyphenyl)propanoateChEBI
2-Hydroxy-3-(p-hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenyllactic acidChEBI
beta-(4-Hydroxyphenyl)lactic acidChEBI
beta-(p-Hydroxyphenyl)lactic acidChEBI
DL-p-Hydroxyphenyllactic acidChEBI
p-Hydroxyphenyl lactic acidChEBI
4-HydroxyphenyllactateKegg
p-HydroxyphenyllactateKegg
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acidGenerator
2-Hydroxy-3-(p-hydroxyphenyl)propionateGenerator
b-(4-Hydroxyphenyl)lactateGenerator
b-(4-Hydroxyphenyl)lactic acidGenerator
beta-(4-Hydroxyphenyl)lactateGenerator
Β-(4-hydroxyphenyl)lactateGenerator
Β-(4-hydroxyphenyl)lactic acidGenerator
b-(p-Hydroxyphenyl)lactateGenerator
b-(p-Hydroxyphenyl)lactic acidGenerator
beta-(p-Hydroxyphenyl)lactateGenerator
Β-(p-hydroxyphenyl)lactateGenerator
Β-(p-hydroxyphenyl)lactic acidGenerator
DL-p-HydroxyphenyllactateGenerator
p-Hydroxyphenyl lactateGenerator
p-Hydroxyphenyllactic acidGenerator
HydroxyphenyllactateGenerator
(RS)-3-(4-Hydroxyphenyl)lactateHMDB
(RS)-3-(4-Hydroxyphenyl)lactic acidHMDB
3-(4-Hydroxyphenyl)-DL-lactateHMDB
3-(4-Hydroxyphenyl)-DL-lactic acidHMDB
3-(4-Hydroxyphenyl)lactateHMDB
3-(p-Hydroxyphenyl)-lactateHMDB
3-(p-Hydroxyphenyl)-lactic acidHMDB
a,4-DihydroxybenzenepropanoateHMDB
a,4-Dihydroxybenzenepropanoic acidHMDB
b-(p-Hydroxyphenyl)-DL-lactateHMDB
b-(p-Hydroxyphenyl)-DL-lactic acidHMDB
beta-(p-Hydroxyphenyl)-DL-lactateHMDB
beta-(p-Hydroxyphenyl)-DL-lactic acidHMDB
DL-3-(4-Hydroxyphenyl)lactateHMDB
DL-3-(4-Hydroxyphenyl)lactic acidHMDB
HPLAHMDB
4-Hydroxyphenyllactic acid, (DL)-isomerHMDB
Para-hydroxyphenyllactic acidHMDB
2-HydroxyphloretateHMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acidHMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid HMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
Traditional Namehydroxyphenyllactic acid
CAS Registry Number306-23-0
SMILES
OC(CC1=CC=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
InChI KeyJVGVDSSUAVXRDY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point414.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility12.9 mg/mL at 16 °CNot Available
LogP0.310 (est)The Good Scents Company Information System
Experimental Chromatographic Properties
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.79 g/LALOGPS
logP10(0.87) g/LALOGPS
logP10(0.88) g/LChemAxon
logS10(-1.6) g/LALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.44 m³·mol⁻¹ChemAxon
Polarizability17.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hydroxyphenyllactic acidOC(CC1=CC=C(O)C=C1)C(O)=O3554.1Standard polar33892256
Hydroxyphenyllactic acidOC(CC1=CC=C(O)C=C1)C(O)=O1782.4Standard non polar33892256
Hydroxyphenyllactic acidOC(CC1=CC=C(O)C=C1)C(O)=O1841.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxyphenyllactic acid,1TMS,isomer #1C[Si](C)(C)OC(CC1=CC=C(O)C=C1)C(=O)O1886.2Semi standard non polar33892256
Hydroxyphenyllactic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(O)C(=O)O)C=C11835.4Semi standard non polar33892256
Hydroxyphenyllactic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)C(O)CC1=CC=C(O)C=C11846.2Semi standard non polar33892256
Hydroxyphenyllactic acid,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C)C(=O)O)C=C11887.2Semi standard non polar33892256
Hydroxyphenyllactic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)O[Si](C)(C)C1884.2Semi standard non polar33892256
Hydroxyphenyllactic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C(O)CC1=CC=C(O[Si](C)(C)C)C=C11856.0Semi standard non polar33892256
Hydroxyphenyllactic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C1910.8Semi standard non polar33892256
Hydroxyphenyllactic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CC1=CC=C(O)C=C1)C(=O)O2132.7Semi standard non polar33892256
Hydroxyphenyllactic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O)C(=O)O)C=C12096.9Semi standard non polar33892256
Hydroxyphenyllactic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=C(O)C=C12101.6Semi standard non polar33892256
Hydroxyphenyllactic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C12386.3Semi standard non polar33892256
Hydroxyphenyllactic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C2338.7Semi standard non polar33892256
Hydroxyphenyllactic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12376.6Semi standard non polar33892256
Hydroxyphenyllactic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2604.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (3 TMS)splash10-004i-1911000000-424dc0a114976e4a60522014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (Non-derivatized)splash10-004i-1911000000-424dc0a114976e4a60522017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxyphenyllactic acid GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-b7f0ddb24f5c187d45402017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-3900000000-aece5a68ba54ab74c5ee2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (3 TMS) - 70eV, Positivesplash10-003r-5496000000-fbb65d0c963e70625e952017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyphenyllactic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00li-2900000000-ea59f9dcf58b55bec6ca2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-054n-9300000000-5b39aa5183630ccd7f4d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0k92-9200000000-c698fdbe1eefac6e9eab2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-01qi-0900000000-640a5a477752571a14432012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid LC-ESI-IT , negative-QTOFsplash10-03di-0900000000-45b5f23bae1a9641fb0b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid LC-ESI-QTOF , negative-QTOFsplash10-01qi-0900000000-640a5a477752571a14432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid , negative-QTOFsplash10-03ei-0900000000-d89828d3625adabd215b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 40V, Positive-QTOFsplash10-00ou-9000000000-60dd6237cac5c79c75082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 10V, Positive-QTOFsplash10-00ri-2900000000-69365cb4d9937f6a96e02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 35V, Negative-QTOFsplash10-00li-1900000000-03a7d2e8f219eba66eee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 35V, Negative-QTOFsplash10-029i-0900000000-fd70bef080a1a354df5a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 20V, Positive-QTOFsplash10-0006-9400000000-65da3c598368dbad66cd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 20V, Positive-QTOFsplash10-052b-9100000000-6ad54b488ac0183ff4bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 10V, Positive-QTOFsplash10-0002-9400000000-af41107b1e7be38f765c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-023a994f4d18e32123cd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 40V, Negative-QTOFsplash10-001i-5900000000-8fcf87adaaae828f3aae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 20V, Negative-QTOFsplash10-00ri-2900000000-ed974245d122fcbc31c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 10V, Negative-QTOFsplash10-03ei-1900000000-fd1d5ff4f32cdcdf0a382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyphenyllactic acid 40V, Negative-QTOFsplash10-00ec-9400000000-9b26dc9e6bb4e1a72cfb2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenyllactic acid 10V, Positive-QTOFsplash10-05o9-0900000000-a343595d5c411e940c252016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenyllactic acid 20V, Positive-QTOFsplash10-0ap0-0900000000-1f777ab6b9486c1813552016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenyllactic acid 40V, Positive-QTOFsplash10-0a6r-9800000000-db82c9bf8afdb32af6de2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenyllactic acid 10V, Negative-QTOFsplash10-001i-2900000000-3e1a7023e9214816e8a52016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenyllactic acid 20V, Negative-QTOFsplash10-052r-2900000000-c05e995d8c57a180bae72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyphenyllactic acid 40V, Negative-QTOFsplash10-05mx-9800000000-729b43ad9499a14c2d012016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.64 +/- 0.24 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified25.10 +/- 14.93 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified17.377 +/- 21.101 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified22.342 +/- 30.410 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified33.513 +/- 76.957 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.55-1.2 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified5.393 +/- 4.849 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified35.939 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.05 +/- 0.43 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified1.1 (0.2-2.6) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0-1.0 umol/mmol creatinineInfant (0-1 year old)Male
Normal
details
UrineDetected and Quantified0-1.0 umol/mmol creatinineInfant (0-1 year old)Female
Normal
details
UrineDetected and Quantified0-2 umol/mmol creatinineInfant (0-1 year old)Male
Normal
details
UrineDetected and Quantified0-2.3 umol/mmol creatinineInfant (0-1 year old)Female
Normal
details
UrineDetected and Quantified3.7 (0.1-11.5) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified4.8 (2.7-5.3) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.51-0.94 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified1.6 (0.3-5.8) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.5 (0.1-8.7) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.0 (0.4-7.3) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified<50.12 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified3.2 (1.5-3.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.8 (2.6-3.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.80 +/- 0.10 uMAdult (>18 years old)BothMorphine treatment details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIleal Crohn's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque details
UrineDetected and Quantified139.639 +/- 122.882 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified74.474 +/- 94.334 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified75.0948 +/- 98.678 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified5.879 +/- 5.443 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified8.512 +/- 4.226 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
UrineDetected and Quantified6.21 +/- 4.38 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified12.6 +/- 36.00 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Phenylketonuria
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
  2. 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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID577
FooDB IDFDB017136
KNApSAcK IDC00050491
Chemspider ID9010
KEGG Compound IDC03672
BioCyc ID4-HYDROXYPHENYLLACTATE
BiGG ID2392410
Wikipedia LinkNot Available
METLIN ID5723
PubChem Compound9378
PDB IDNot Available
ChEBI ID17385
Food Biomarker OntologyNot Available
VMH ID34HPL
MarkerDB IDMDB00029989
Good Scents IDrw1622271
References
Synthesis ReferenceDeng, Xi-ling; Wang, Xin-bing; Xiang, Ying; Zhu, Shi-fa. Synthesis of b-(4-hydroxyphenyl)lactic acid. Shihezi Daxue Xuebao, Ziran Kexueban (2005), 23(1), 11-13.
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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. 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 ]
  3. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
  4. Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. [PubMed:1444166 ]
  5. Roth K, Cohn R, Yandrasitz J, Preti G, Dodd P, Segal S: Beta-methylcrotonic aciduria associated with lactic acidosis. J Pediatr. 1976 Feb;88(2):229-35. [PubMed:1249684 ]
  6. Spaapen LJ, Ketting D, Wadman SK, Bruinvis L, Duran M: Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin. J Inherit Metab Dis. 1987;10(4):383-90. [PubMed:3126358 ]
  7. Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. [PubMed:9106023 ]
  8. Mrochek JE, Dinsmore SR, Ohrt DW: Monitoring phenylalanine-tyrosine metabolism by high-resolution liquid chromatography of urine. Clin Chem. 1973 Aug;19(8):927-36. [PubMed:4720815 ]
  9. Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738 ]
  10. Jakobs C, Sweetman L, Nyhan WL: Chemical analysis of succinylacetone and 4-hydroxyphenyllactate in amniotic fluid using selective ion monitoring. Prenat Diagn. 1984 May-Jun;4(3):187-94. [PubMed:6463026 ]
  11. Beloborodova N, Bairamov I, Olenin A, Shubina V, Teplova V, Fedotcheva N: Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils. J Biomed Sci. 2012 Oct 12;19:89. doi: 10.1186/1423-0127-19-89. [PubMed:23061754 ]
  12. Beloborodova NV, Khodakova AS, Bairamov IT, Olenin AY: Microbial origin of phenylcarboxylic acids in the human body. Biochemistry (Mosc). 2009 Dec;74(12):1350-5. [PubMed:19961416 ]
  13. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  14. (). Charles Scriver, Arthur Beaudet, William Sly, David Valle, Barton Childs, Kenneth Kinzler, Bert Vogelstein. The Metabolic and Molecular Bases of Inherited Disease. McGraw-Hill Professional; 8 edition (Dec 15 2000). . . [ISBN:978-0079130358 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Hydroxyphenyllactic acid → 3-(4-hydroxyphenyl)-2-(sulfooxy)propanoic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Hydroxyphenyllactic acid → 6-[4-(2-carboxy-2-hydroxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Hydroxyphenyllactic acid → 3,4,5-trihydroxy-6-{[2-hydroxy-3-(4-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Hydroxyphenyllactic acid → 2-hydroxy-3-[4-(sulfooxy)phenyl]propanoic aciddetails