(2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acid

• ChemBase ID: 1729
• Molecular Formular: C9H12NO6P
• Molecular Mass: 261.168441
• Monoisotopic Mass: 261.04022374
• SMILES: N[C@@H](Cc1ccc(OP(=O)(O)O)cc1)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(cc1)OP(=O)(O)O)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
• InChIKey: DCWXELXMIBXGTH-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acid
• IUPAC Traditional name: phosphonotyrosine
• Synonyms: L-3-(4-Hydroxyphenyl)alanine 4’-Phosphate; Phosphotyrosine; O-Phospho-L-tyrosine; L-3-(4-Hydroxyphenyl)alanine 4′-phosphate; L-Tyrosine-O-phosphate; O-Phospho-L-tyrosine; Phosphonotyrosine

Database IDs

• CAS Number: 21820-51-9
• MDL Number: MFCD00002603
• Beilstein Number: 3150815
• PubChem SID: 24899034; 160965185; 46507690
• PubChem CID: 30819

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.3784037
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.2425585
• LogD (pH = 7.4): -5.104805
• Log P: -1.5143896
• Molar Refractivity: 57.9701 cm^3
• Polarizability: 22.964252 Å^3
• Polar Surface Area: 130.08 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.76
• LOG S: -2.13
• Solubility (Water): 1.93e+00 g/l

PROPERTIES

Physical Property

• Solubility: Butanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 226-227°C
• Optical Rotation: [α]20/D -5.5±0.5°, c = 1% in 2 M HCl

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~95% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C9H12NO6P

DETAILS

DrugBank - DB01962

• Drug Groups: experimental
• Description: An amino acid that occurs in endogenous proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis. [PubChem]

Sigma Aldrich - 79720

Other Notes
Detection and quantification of phosphotyrosine in proteins1

Toronto Research Chemicals - P365000

Useful in the study of tyrosine-phosphorylation, which has been linked with the malignant transformation of cells by some RNA tumour viruses.

REFERENCES

• Sefton, B.M., et al.: Cell, 20, 807 (1980)
• Erikson, R., et al.: Perspect. Virol., 11, 93 (1980)
• Lee, E-S, et al.: J. Org. Chem., 59, 2086 (1994)