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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-04-03 14:10:30 UTC
Update Date2023-07-07 20:54:00 UTC
HMDB IDHMDB0013678
Secondary Accession Numbers
  • HMDB13678
Metabolite Identification
Common Namep-Hydroxyhippuric acid
Description4-Hydroxyhippuric acid, also known as 4-hydroxybenzoylglycine or 4-hydroxyhippate, belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. 4-Hydroxyhippuric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Hydroxyhippuric acid.
Structure
Data?1676999880
Synonyms
ValueSource
4-HydroxybenzoylglycineChEBI
4-HydroxyhippateGenerator
4-Hydroxyhippic acidGenerator
2-[(4-Hydroxyphenyl)carbonylamino]acetic acidHMDB
2-[(4-Hydroxyphenyl)formamido]acetic acidHMDB
4-HydroxyhippurateHMDB
4-OH-Hippuric acidHMDB
p-Hydroxy-hippuric acidHMDB
[(4-Hydroxybenzoyl)amino]acetic acidHMDB
p-Hydroxyhippuric acidHMDB
p-HydroxyhippateHMDB
p-Hydroxyhippic acidHMDB
4'-HydroxyhippurateHMDB
4'-Hydroxyhippuric acidHMDB
4’-hydroxyhippurateHMDB
4’-hydroxyhippuric acidHMDB
N-(p-Hydroxybenzoyl)glycineHMDB
p-HydroxyhippurateHMDB
4-Hydroxyhippuric acidChEBI
2-[(4-Hydroxybenzoyl)amino]acetic acidHMDB
4'-Hydroxhippuric acidHMDB
Chemical FormulaC9H9NO4
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
IUPAC Name2-[(4-hydroxyphenyl)formamido]acetic acid
Traditional Name[(4-hydroxyphenyl)formamido]acetic acid
CAS Registry Number2482-25-9
SMILES
OC(=O)CNC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H9NO4/c11-7-3-1-6(2-4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
InChI KeyZMHLUFWWWPBTIU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.63 g/LALOGPS
logP0.44ALOGPS
logP0.22ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.1 m³·mol⁻¹ChemAxon
Polarizability18.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.44631661259
DarkChem[M-H]-142.58631661259
DeepCCS[M+H]+138.92830932474
DeepCCS[M-H]-136.53230932474
DeepCCS[M-2H]-171.73130932474
DeepCCS[M+Na]+146.24830932474
AllCCS[M+H]+141.832859911
AllCCS[M+H-H2O]+137.832859911
AllCCS[M+NH4]+145.632859911
AllCCS[M+Na]+146.732859911
AllCCS[M-H]-141.432859911
AllCCS[M+Na-2H]-142.032859911
AllCCS[M+HCOO]-142.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxyhippuric acidOC(=O)CNC(=O)C1=CC=C(O)C=C13281.9Standard polar33892256
4-Hydroxyhippuric acidOC(=O)CNC(=O)C1=CC=C(O)C=C12044.3Standard non polar33892256
4-Hydroxyhippuric acidOC(=O)CNC(=O)C1=CC=C(O)C=C12209.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyhippuric acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)C1=CC=C(O)C=C12145.7Semi standard non polar33892256
4-Hydroxyhippuric acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(C(=O)NCC(=O)O)C=C12149.8Semi standard non polar33892256
4-Hydroxyhippuric acid,1TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=C(O)C=C12108.3Semi standard non polar33892256
4-Hydroxyhippuric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)C1=CC=C(O[Si](C)(C)C)C=C12258.9Semi standard non polar33892256
4-Hydroxyhippuric acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O)C=C1)[Si](C)(C)C2153.3Semi standard non polar33892256
4-Hydroxyhippuric acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C)C=C12140.2Semi standard non polar33892256
4-Hydroxyhippuric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2147.5Semi standard non polar33892256
4-Hydroxyhippuric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2106.7Standard non polar33892256
4-Hydroxyhippuric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2233.8Standard polar33892256
4-Hydroxyhippuric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=C(O)C=C12390.8Semi standard non polar33892256
4-Hydroxyhippuric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)NCC(=O)O)C=C12427.6Semi standard non polar33892256
4-Hydroxyhippuric acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=C(O)C=C12385.1Semi standard non polar33892256
4-Hydroxyhippuric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12778.8Semi standard non polar33892256
4-Hydroxyhippuric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2653.3Semi standard non polar33892256
4-Hydroxyhippuric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C=C12687.1Semi standard non polar33892256
4-Hydroxyhippuric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2885.4Semi standard non polar33892256
4-Hydroxyhippuric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2739.4Standard non polar33892256
4-Hydroxyhippuric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2595.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxyhippuric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1900000000-07bd47210e1c18d19c782017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxyhippuric acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-8982000000-016ad8c26c264db9ef972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxyhippuric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxyhippuric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxyhippuric acid 35V, Negative-QTOFsplash10-0f6x-9400000000-3d4dbdacafaebba147cf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxyhippuric acid 35V, Positive-QTOFsplash10-00di-0900000000-a916e7c30b53b399298a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 10V, Positive-QTOFsplash10-006t-0900000000-d252a86f47419d419bc02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 20V, Positive-QTOFsplash10-00di-1900000000-a680ce571986b15d0d712016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 40V, Positive-QTOFsplash10-00dl-9600000000-39500903a2246ed4d7d82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 10V, Negative-QTOFsplash10-0006-0900000000-f6ed56b2505b426ab18b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 20V, Negative-QTOFsplash10-0006-2900000000-0c2b762b727ebf3108f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 40V, Negative-QTOFsplash10-00dl-9200000000-cfd75bbf2139a9e184ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 10V, Negative-QTOFsplash10-0006-9600000000-677e373389c304ac33e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 20V, Negative-QTOFsplash10-0006-9100000000-4edfd065383ed838da2f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 40V, Negative-QTOFsplash10-0006-9000000000-983418779545bcb1f73e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 10V, Positive-QTOFsplash10-00di-4900000000-9c98bf04ba07933f98aa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 20V, Positive-QTOFsplash10-00di-3900000000-d3d1bc473b13420cae0c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxyhippuric acid 40V, Positive-QTOFsplash10-01bc-9200000000-4b8b59c1ab3079b9b3d02021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1.691 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1.742 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1.793 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified4.0989 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.369 (0.0461-1.0350) nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0-14 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Great Plains Labo...
details
UrineDetected and Quantified0-30 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Great Plains Labo...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.2-19.59 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified7.42(4.69-18.33) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified7.48(4.17-19.96) umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified2.8 (1.4-6.0) umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified27.488 +/- 10.23 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified4.55 (3.40-7.47) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified93.846 +/- 33.846 uMAdult (>18 years old)Both
Uremia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified35.234 +/- 16.83 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified35.795 +/- 21.952 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Colorectal cancer
  1. 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 ]
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 IDNot Available
FooDB IDFDB029984
KNApSAcK IDC00052156
Chemspider ID133104
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151012
PDB IDNot Available
ChEBI ID71018
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029845
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jacobs DM, Spiesser L, Garnier M, de Roo N, van Dorsten F, Hollebrands B, van Velzen E, Draijer R, van Duynhoven J: SPE-NMR metabolite sub-profiling of urine. Anal Bioanal Chem. 2012 Nov;404(8):2349-61. doi: 10.1007/s00216-012-6339-2. Epub 2012 Aug 31. [PubMed:22932811 ]
  2. van Duynhoven J, Vaughan EE, Jacobs DM, Kemperman RA, van Velzen EJ, Gross G, Roger LC, Possemiers S, Smilde AK, Dore J, Westerhuis JA, Van de Wiele T: Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci U S A. 2011 Mar 15;108 Suppl 1:4531-8. doi: 10.1073/pnas.1000098107. Epub 2010 Jun 25. [PubMed:20615997 ]
  3. 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 ]