Phospho-L-tyrosine

HCID 30819

Substructure search Find similar structures

Basic information

CAS: 21820-51-9
Standard SMILES: N[C@@H](Cc1ccc(OP(=O)(O)O)cc1)C(=O)O
InChIKey: DCWXELXMIBXGTH-QMMMGPOBSA-N
Molecular formula: C9H12NO6P
Average molar mass: 261.17 g/mol
Monoisotopic mass: 261.04022373

Overview

O(4)-phospho-L-tyrosine is a non-proteinogenic L-alpha-amino acid that is L-tyrosine phosphorylated at the phenolic hydroxy group. It has a role as an immunogen and an Escherichia coli metabolite. It is a L-tyrosine derivative, an O(4)-phosphotyrosine and a non-proteinogenic L-alpha-amino acid. It is a conjugate acid of an O(4)-phosphonato-L-tyrosine(2-). It is an enantiomer of an O(4)-phospho-D-tyrosine.

Names & identifiers

Preferred name: Phospho-L-tyrosine
IUPAC: (2S)-2-amino-3-(4-phosphonooxyphenyl)propanoic acid
English name: O-Phospho-L-tyrosine
Molecular formula: C9H12NO6P
Molecular weight: 261.17

Names & synonyms

21820-51-9PhosphonotyrosinePHOSPHOTYROSINEPhospho-L-tyrosine2R86C98KDXDTXSID00176234L-Tyrosine, dihydrogen phosphate (ester)(2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acid(2S)-2-amino-3-(4-(phosphonooxy)phenyl)propanoic acidtyrosine-o-phosphateTyrosine O phosphateRefChem:863006

Show more names

p-TyrH-TYR(P)-OHPhospho-TyrH-Tyr(PO3)-OHH-TYR(PO3H2)-OHL-Tyr(H2PO3)-OHH-L-Tyr(PO3H2)-OH

DTXCID9098725O-Phospho-L-tyrosineO-PhosphotyrosineH-Tyr(H2PO3)-OHL-Tyrosine-O-phosphateTyrosine O-phosphateO-phosphono-L-tyrosineL-Phosphotyrosine

Database identifiers

CAS: 21820-51-9
PubChem CID: 30819
DTXSID: DTXSID00176234
ChEMBL: CHEMBL286939
ChEBI: CHEBI:37788
UNII: 2R86C98KDX
EC Number: 891-585-9
Nikkaji: J208.898C

Properties

Computed structural properties

XLogP: -2.8
Topological polar surface area: 130 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 7
Rotatable bonds: 5
Heavy atoms: 17
Formal charge: 0
Complexity: 309

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives

DrugsPharmaceuticals -> Listed in ZINC15

Physical Description · 2 items

White solid; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section149.33 Å² [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Melting point: 226 · 226-227°C
Boiling point: 521.7 · 521.7±60.0 °C(Predicted)
Density: 1.591 · 1.591±0.06 g/cm3(Predicted)
storage temp.: -20 °C · Sealed in dry,Store in freezer, under -20°C
solubility: Aqueous Acid (Slightly), Water (Slightly, Sonicated)
form: Solid
pka: 1.24 · 1.24±0.30(Predicted)
color: White to Off-White
optical activity: -9.6 ° · -9.6° (C=0.01 g/ml, 1N HCL)
BRN: 3150815 · 3150815
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
InChIKey: DCWXELXMIBXGTH-QMMMGPOBSA-N
SMILES: N[C@@H](Cc1ccc(OP(O)(O)=O)cc1)C(O)=O
CAS DataBase Reference: 21820 · 21820-51-9(CAS DataBase Reference)
FDA UNII: 2 R86C98KDX · 2R86C98KDX
UNSPSC Code: 12352209 · 12352209
NACRES: 26 · NA.26
Hazard Codes: Xn
Risk Statements: 21 · 21/22
Safety Statements: 36 · 36/37
WGK Germany: 3 · 3
F: 10 · 10-21
HS Code: 29225090 · 29225090
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.

Not Classified

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationStatus: Active Update: 04-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/34754

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesNot Classified

Safety data

F: 10-21
wgk: 3
hs_code: 29225090
risk_code: 21/22
hazard_code: Xn
safety_code: 36/37
Storage Class: 11 - Combustible Solids
REACH Registrations: Active

Chemistry & industry

Uses & manufacturing

UsesAmino acid found in endogenous proteins; [ChemIDplus]

Applications

UsesO-Phospho-L-tyrosine is used in the study of tyrosine-phosphorylation, which has been linked to the malignant transformation of cells by various RNA tumor viruses. Plays a role in signal transduction.