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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:05:31 UTC
Update Date2023-02-21 17:26:43 UTC
HMDB IDHMDB0038750
Secondary Accession Numbers
  • HMDB38750
Metabolite Identification
Common NameN-Hydroxy-L-tyrosine
DescriptionN-Hydroxy-L-tyrosine belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Hydroxy-L-tyrosine has been detected, but not quantified in, several different foods, such as capers (Capparis spinosa), tindas (Citrullus lanatus var. fistulosus), garden tomato (var.), agaves (Agave), and hedge mustards (Sisymbrium). This could make N-hydroxy-L-tyrosine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Hydroxy-L-tyrosine.
Structure
Data?1677000403
Synonyms
ValueSource
(2S)-2-(hydroxyamino)-3-(4-Hydroxyphenyl)propanoic acidHMDB
N-HydroxytyrosineHMDB
2-(N-Hydroxyamino)-3-(4-hydroxyphenyl)propanoateGenerator
Chemical FormulaC9H11NO4
Average Molecular Weight197.1879
Monoisotopic Molecular Weight197.068807845
IUPAC Name2-(N-hydroxyamino)-3-(4-hydroxyphenyl)propanoic acid
Traditional Name2-(N-hydroxyamino)-3-(4-hydroxyphenyl)propanoic acid
CAS Registry Number64448-49-3
SMILES
ONC(CC1=CC=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H11NO4/c11-7-3-1-6(2-4-7)5-8(10-14)9(12)13/h1-4,8,10-11,14H,5H2,(H,12,13)
InChI KeyCNIUEVQJABPUIJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • N-hydroxyl-alpha-amino acid
  • Amphetamine or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • N-organohydroxylamine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateNot Available
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 Solubility5.08 g/LALOGPS
logP-0.31ALOGPS
logP0.38ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.42ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.35 m³·mol⁻¹ChemAxon
Polarizability18.89 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]+146.37531661259
DarkChem[M-H]-143.53531661259
DeepCCS[M+H]+139.52930932474
DeepCCS[M-H]-135.70230932474
DeepCCS[M-2H]-173.2230932474
DeepCCS[M+Na]+148.75930932474
AllCCS[M+H]+144.032859911
AllCCS[M+H-H2O]+139.932859911
AllCCS[M+NH4]+147.832859911
AllCCS[M+Na]+148.932859911
AllCCS[M-H]-141.332859911
AllCCS[M+Na-2H]-141.932859911
AllCCS[M+HCOO]-142.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Hydroxy-L-tyrosineONC(CC1=CC=C(O)C=C1)C(O)=O3645.1Standard polar33892256
N-Hydroxy-L-tyrosineONC(CC1=CC=C(O)C=C1)C(O)=O1965.3Standard non polar33892256
N-Hydroxy-L-tyrosineONC(CC1=CC=C(O)C=C1)C(O)=O2122.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Hydroxy-L-tyrosine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC(NO)C(=O)O)C=C12045.0Semi standard non polar33892256
N-Hydroxy-L-tyrosine,1TMS,isomer #2C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)NO2020.3Semi standard non polar33892256
N-Hydroxy-L-tyrosine,1TMS,isomer #3C[Si](C)(C)N(O)C(CC1=CC=C(O)C=C1)C(=O)O2069.3Semi standard non polar33892256
N-Hydroxy-L-tyrosine,2TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)NO2013.4Semi standard non polar33892256
N-Hydroxy-L-tyrosine,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(C(=O)O)N(O)[Si](C)(C)C)C=C12088.2Semi standard non polar33892256
N-Hydroxy-L-tyrosine,2TMS,isomer #3C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)N(O)[Si](C)(C)C2056.5Semi standard non polar33892256
N-Hydroxy-L-tyrosine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)N(O)[Si](C)(C)C2070.2Semi standard non polar33892256
N-Hydroxy-L-tyrosine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)N(O)[Si](C)(C)C1985.4Standard non polar33892256
N-Hydroxy-L-tyrosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC(NO)C(=O)O)C=C12306.5Semi standard non polar33892256
N-Hydroxy-L-tyrosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)NO2275.5Semi standard non polar33892256
N-Hydroxy-L-tyrosine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(O)C(CC1=CC=C(O)C=C1)C(=O)O2325.2Semi standard non polar33892256
N-Hydroxy-L-tyrosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)NO2555.5Semi standard non polar33892256
N-Hydroxy-L-tyrosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)O)N(O)[Si](C)(C)C(C)(C)C)C=C12633.3Semi standard non polar33892256
N-Hydroxy-L-tyrosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)N(O)[Si](C)(C)C(C)(C)C2547.2Semi standard non polar33892256
N-Hydroxy-L-tyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(O)[Si](C)(C)C(C)(C)C2807.6Semi standard non polar33892256
N-Hydroxy-L-tyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(O)[Si](C)(C)C(C)(C)C2636.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Hydroxy-L-tyrosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3900000000-be5de665f715625b95f62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Hydroxy-L-tyrosine GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-4492000000-9e70ef37c06108fc4e1d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Hydroxy-L-tyrosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 10V, Positive-QTOFsplash10-0532-0900000000-bfdf24beb417c2dacbb72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 20V, Positive-QTOFsplash10-0a4i-0900000000-8ac5e421f1523b71191a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 40V, Positive-QTOFsplash10-0a6r-9800000000-91cd85dd0e0d8fa57b6c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 10V, Negative-QTOFsplash10-0002-2900000000-646d7b71fb495968b55e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 20V, Negative-QTOFsplash10-0007-9700000000-ce87dccb8aefac5e4f7b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 40V, Negative-QTOFsplash10-05tf-9500000000-cc1ecac33062a1cd08262015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 10V, Negative-QTOFsplash10-016r-0900000000-f6bb36ced8e895f40ad02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 20V, Negative-QTOFsplash10-014i-2900000000-bb6e7acaec05e0bd98de2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 40V, Negative-QTOFsplash10-00kf-9800000000-4cd08ed122072d18b6f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 10V, Positive-QTOFsplash10-0f6t-0900000000-664b046027f7ed01fd802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 20V, Positive-QTOFsplash10-0a4i-0900000000-4fc84b71c4dbbbb7e5f62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Hydroxy-L-tyrosine 40V, Positive-QTOFsplash10-05r3-9300000000-65c757724b29d767f3962021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018162
KNApSAcK IDNot Available
Chemspider ID3676057
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4478048
PDB IDNot Available
ChEBI ID28089
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .