Record Information
Version2.0
Creation Date2012-07-30 14:55:11 -0600
Update Date2015-06-03 17:21:04 -0600
Secondary Accession Numbers
  • ECMDB21276
Identification
Name:Phosphotyrosine
Description:Phosphotyrosine is a tyrosine (an amino acid) with a phosphate attached to its aromatic ring. Tyrosine (abbreviated as Tyr or Y) is one of the 22 amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. (Wikipedia) Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control. (PubChem) In E. coli, phosphotyrosine can act as a noncompetitive inhibitor of the enzyme biosynthetic ornithine decarboxylase. (EcoCyc)
Structure
Thumb
Synonyms:
  • (S)-2-amino-3-(4-hydroxyphenyl)propanoate 4'-phosphate
  • (S)-2-amino-3-(4-hydroxyphenyl)propanoic acid 4'-phosphate
  • (S)-2-amino-3-(4-Hydroxyphenyl)propanoic acid 4'-phosphoric acid
  • L-3-(4-Hydroxyphenyl)alanine 4'-phosphate
  • L-3-(4-Hydroxyphenyl)alanine 4'-phosphoric acid
  • L-Phosphotyrosine
  • L-Tyrosine, dihydrogen phosphate (ester)
  • L-Tyrosine, dihydrogen phosphoric acid (ester)
  • L-Tyrosine-O-phosphate
  • L-Tyrosine-O-phosphoric acid
  • O-Phospho-L-tyrosine
  • O-Phosphono-L-tyrosine
  • O-Phosphotyrosine
  • O4'-phospho-L-tyrosine
  • O4-phosphono-L-tyrosine
  • O4-phosphotyrosine
  • Phospho-L-tyrosine
  • Phosphonotyrosine
  • Phosphotyrosine
  • Phosphotyrosine (pY)
  • Tyrosine O-phosphate
  • Tyrosine O-phosphoric acid
  • Tyrosine phosphate
  • Tyrosine phosphoric acid
Chemical Formula:C9H12NO6P
Weight:Average: 261.1684
Monoisotopic: 261.040223633
InChI Key:DCWXELXMIBXGTH-QMMMGPOBSA-N
InChI: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
CAS number:21820-51-9
IUPAC Name:(2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acid
Traditional IUPAC Name:phosphonotyrosine
SMILES:N[C@@H](CC1=CC=C(OP(O)(O)=O)C=C1)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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 ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Phenyl phosphate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amphetamine or derivatives
  • Aryl phosphomonoester
  • Aryl phosphate
  • Phenoxy compound
  • Aralkylamine
  • Phosphoric acid ester
  • Monocyclic benzene moiety
  • Organic phosphoric acid derivative
  • Benzenoid
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.93 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.97 m³·mol⁻¹ChemAxon
Polarizability22.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
tyrosine biosynthesisPW000806 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kv-9760000000-fac0ad90cc9632ea6e27View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-7490000000-942403f966393fcd98dfView in MoNA
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
References
References:
  • 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. Pubmed: 7516161
  • Kataoka, H., Nakai, K., Katagiri, Y., Makita, M. (1993). "Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection." Biomed Chromatogr 7:184-188. Pubmed: 7693088
  • 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. Pubmed: 1282059
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID37788
HMDB IDHMDB06049
Pubchem Compound ID30819
Kegg IDC06501
ChemSpider ID28593
WikipediaPhosphotyrosine
BioCyc IDCPD-3728
EcoCyc IDCPD-3728
Ligand ExpoPTR

Enzymes

General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
appA
Uniprot ID:
P07102
Molecular weight:
47056
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
Myo-inositol hexakisphosphate + H(2)O = 1D-myo-inositol 1,2,3,5,6-pentakisphosphate + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:
aphA
Uniprot ID:
P0AE22
Molecular weight:
26103
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368