2-amino-3-(4-amino-3-hydroxyphenyl)propanoic acid

• ChemBase ID: 160535
• Molecular Formular: C9H12N2O3
• Molecular Mass: 196.20318
• Monoisotopic Mass: 196.08479225
• SMILES: c1c(c(cc(c1)CC(N)C(=O)O)O)N
• Canonical SMILES: OC(=O)C(Cc1ccc(c(c1)O)N)N
• InChI: InChI=1S/C9H12N2O3/c10-6-2-1-5(4-8(6)12)3-7(11)9(13)14/h1-2,4,7,12H,3,10-11H2,(H,13,14)
• InChIKey: XHWPXBNFKWLGJH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(4-amino-3-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: 2-amino-3-(4-amino-3-hydroxyphenyl)propanoic acid
• Synonyms: 4-Amino-3-hydroxyphenylalanine Dihydrochloride; rac 4-Amino-m-tyrosine Dihydrochloride

Database IDs

• CAS Number: 21819-90-9
• PubChem SID: 162254670
• PubChem CID: 23253805

CALCULATED PROPERTIES

• Acid pKa: 1.2413372
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.470696
• LogD (pH = 7.4): -2.3240879
• Log P: -2.3252165
• Molar Refractivity: 51.7976 cm^3
• Polarizability: 19.671629 Å^3
• Polar Surface Area: 109.57 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A632020

4-Amino-m-tyrosine is a degradation product of Pheomelanin, a compound found in hair and skin in humans.

REFERENCES

• Patil, D. et al.: J. Org. Chem., 49, 997 (1984)
• Fattorusso, E. et al.: Gazz. Chem. Ital., 98, 1443 (1984)