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Record Information
Version3.6
Creation Date2007-04-12 21:15:42 UTC
Update Date2016-02-11 01:07:21 UTC
HMDB IDHMDB06049
Secondary Accession NumbersNone
Metabolite Identification
Common NameO-Phosphotyrosine
DescriptionO-Phosphotyrosine is a phosphorylated amino acid that occurs in a number of proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis. Small amounts of free phosphotyrosine can be found in urine (PMID: 7693088 ). Levels of this amino acid appear to be elevated in mammalian urine during liver regeneration (PMID: 7516161 ). Phosphotyrosine is also able to induce platelet aggregation in vitro and it has been suggested that free phosphotyrosine in blood could be meaningful for in vivo platelet activation (PMID: 1282059 ).
Structure
Thumb
Synonyms
ValueSource
PhosphonotyrosineKegg
L-PhosphotyrosineHMDB
L-3-(4-Hydroxyphenyl)alanine 4'-phosphateHMDB
L-Tyrosine-O-phosphateHMDB
O-phospho-L-TyrosineHMDB
phospho-L-TyrosineHMDB
PhosphotyrosineHMDB
Phosphotyrosine (py)HMDB
Tyrosine O-phosphateHMDB
Chemical FormulaC9H12NO6P
Average Molecular Weight261.1684
Monoisotopic Molecular Weight261.040223633
IUPAC Name(2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acid
Traditional Namephosphonotyrosine
CAS Registry NumberNot Available
SMILES
N[C@@H](CC1=CC=C(OP(O)(O)=O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H12NO6P/c10-8(9(11)12)5-6-1-3-7(4-2-6)16-17(13,14)15/h1-4,8H,5,10H2,(H,11,12)(H2,13,14,15)/t8-/m0/s1
InChI KeyInChIKey=DCWXELXMIBXGTH-QMMMGPOBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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
  • L-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Aralkylamine
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Cell Signaling
  • Signal transduction
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.93 mg/mLALOGPS
logP-0.76ALOGPS
logP-1.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.38ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area130.08 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.97 m3·mol-1ChemAxon
Polarizability22.7 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02td-1190000000-c4bdb7da24563b4177c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1790000000-55cef97dac3a8d00ae8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-1f6422b48ae626b43485View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9030000000-8821df5eb9bab97574d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-52223829a773b1820856View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0e7b4ff762027c709269View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.00073 +/- 0.00005 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023821
KNApSAcK IDNot Available
Chemspider ID28593
KEGG Compound IDC06501
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06049
Metagene LinkHMDB06049
METLIN IDNot Available
PubChem Compound30819
PDB IDPTR
ChEBI ID37788
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kataoka H, Nakai K, Katagiri Y, Makita M: Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection. Biomed Chromatogr. 1993 Jul-Aug;7(4):184-8. [7693088 ]
  2. Kataoka H, Nakai K, Makita M: Increase of phosphotyrosine levels in mouse urine and liver during liver regeneration after partial hepatectomy. Biochem Biophys Res Commun. 1994 Jun 15;201(2):909-16. [7516161 ]
  3. Munoz GE, Arenas-Diaz G, Marshall SH: Exogenously added free phosphotyrosine induces aggregation of circulating platelets in rabbits. Cell Mol Biol (Noisy-le-grand). 1992 Nov;38(7):719-22. [1282059 ]