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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:11 -0600
Update Date	2015-06-03 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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xaacce5ac> Close
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
Description	belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives 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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Phenylalanine and derivatives
Alternative Parents	Phenylpropanoic acids Phenyl phosphates L-alpha-amino acids Amphetamines and derivatives Phenoxy compounds Aralkylamines Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aromatic homomonocyclic compounds
External Descriptors	non-proteinogenic L-alpha-amino acid (CHEBI:37788 ) L-tyrosine derivative (CHEBI:37788 ) O(4)-phosphotyrosine (CHEBI:37788 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 1.93 g/L ALOGPS logP -0.76 ALOGPS logP -1.5 ChemAxon logS -2.1 ALOGPS pKa (Strongest Acidic) 1.38 ChemAxon pKa (Strongest Basic) 9.46 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 130.08 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 57.97 m³·mol⁻¹ ChemAxon Polarizability 22.7 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Water + Phosphotyrosine > Phosphate + L-Tyrosine
SMPDB Pathways:	tyrosine biosynthesis PW000806
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-00kv-9760000000-fac0ad90cc9632ea6e27 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-014i-7490000000-942403f966393fcd98df View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-02td-1190000000-c4bdb7da24563b4177c3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014j-1790000000-55cef97dac3a8d00ae8e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-2900000000-1f6422b48ae626b43485 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-9030000000-8821df5eb9bab97574d6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9110000000-52223829a773b1820856 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-0e7b4ff762027c709269 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-9060000000-ccb200a7330d4d29af62 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-a5e502a2627af2048a1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-a5e502a2627af2048a1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-02t9-0090000000-813cf20537b120ee03f1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014j-1190000000-30d2bc5ccbdd91a0b720 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-3910000000-6669265710f2d4346cd6 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 37788 HMDB ID HMDB06049 Pubchem Compound ID 30819 Kegg ID C06501 ChemSpider ID 28593 Wikipedia Phosphotyrosine BioCyc ID CPD-3728 EcoCyc ID CPD-3728 Ligand Expo PTR

Enzymes

Transporters