(2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid

• ChemBase ID: 170412
• Molecular Formular: C9H11NO5
• Molecular Mass: 213.18734
• Monoisotopic Mass: 213.06372246
• SMILES: c1c(c(cc(c1C[C@H](N)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@H](Cc1cc(O)c(cc1O)O)N
• InChI: InChI=1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)/t5-/m0/s1
• InChIKey: YLKRUSPZOTYMAT-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid
• IUPAC Traditional name: 2,4,5-trihydroxyphenylalanine
• Synonyms: 2,4,5-Trihydroxy-L-phenylalanine; 2,4,5-Trihydroxyphenylalanine; 2,5-Dihydroxy-L-tyrosine; 3-(3,4,6-Trihydroxyphenyl)-L-alanine; 6-Hydroxy-L-DOPA; Hydroxy-L-dopa; L-6-Hydroxydopa; TOPA; 6-Hydroxy-L-DOPA

Database IDs

• CAS Number: 27244-64-0
• PubChem SID: 164226322
• PubChem CID: 33755

CALCULATED PROPERTIES

• Acid pKa: 1.3455039
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.0957322
• LogD (pH = 7.4): -2.1093547
• Log P: -2.095667
• Molar Refractivity: 51.059 cm^3
• Polarizability: 19.826963 Å^3
• Polar Surface Area: 124.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941725

6-Hydroxy-L-DOPA is the 6-hydroxy derivative of the amino acid L-DOPA (D533751) with neurotoxic properties. Studies show that exogenously administered 6-Hydroxy-L-DOPA is biotransformed by amino acid decarboxylase to the highly potent and catecholamine-se

REFERENCES

• Jaim-Etcheverry, G. et al.: Brain Res., 100, 699 (1975)
• Kostrzewa, R.M. et al.: Amino Acids, 14, 175 (1975)
• Berthet, A. et al.: J. Neurosci., 29, 4829 (1975)