(2S)-2-amino-3-(3-hydroxyphenyl)propanoic acid

• ChemBase ID: 2128
• Molecular Formular: C9H11NO3
• Molecular Mass: 181.18854
• Monoisotopic Mass: 181.07389322
• SMILES: N[C@@H](Cc1cccc(O)c1)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1cccc(c1)O)N
• InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-2-1-3-7(11)4-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1
• InChIKey: JZKXXXDKRQWDET-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(3-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: meta-tyrosine; 3-hydroxyphenylalanine
• Synonyms: 3-Hydroxy-L-phenylalanine; 3-(m-Hydroxyphenyl)alanine; 3-Hydroxyphenylalanine; L-meta-Tyrosine; m-L-Tyrosine; L-m-Tyrosine; 3-(3-Hydroxyphenyl)-L-alanine; H-Phe(3-OH)-OH; L-m-Tyrosine; Meta-Tyrosine; 3-Hydroxyphenylalanine; (S)-2-Amino-3-(3-hydroxyphenyl)propanoic acid; L-m-酪氨酸

Database IDs

• CAS Number: 587-33-7
• MDL Number: MFCD00063059
• PubChem SID: 46505633; 46507251; 160965582
• PubChem CID: 6950578

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.0020301
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.488467
• LogD (pH = 7.4): -1.4959543
• Log P: -1.4885992
• Molar Refractivity: 47.0972 cm^3
• Polarizability: 18.512545 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.34
• LOG S: -1.55
• Solubility (Water): 5.13e+00 g/l

PROPERTIES

Physical Property

• Solubility: Dilute Acid; DMSO
• Apperance: Pale Beige Solid
• Melting Point: 260-270°C; 267-270°C (dec)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• TSCA Listed: 否

Product Information

• Purity: 97%; 97+%

DETAILS

DrugBank - DB02387

Drug information: experimental

DrugBank - DB03552

Drug information: experimental

Toronto Research Chemicals - T910010

It is an unnatural amino acid ; shown application in the treatment of Parkinson’s disease, Alzheimer’s disease, artritis.

REFERENCES

• Hollunge, G., et al.: Acta Pharmacol. Toxicol., 34, 391 (1974)
• Fell, V., et al.: Biochem. Med., 22, 246 (1974)
• Isono, F., et al.: J. Antibiot., 42, 667 (1974)