(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid

• ChemBase ID: 1531
• Molecular Formular: C9H10INO3
• Molecular Mass: 307.08507
• Monoisotopic Mass: 306.97054119
• SMILES: N[C@@H](Cc1ccc(O)c(I)c1)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(c(c1)I)O)N
• InChI: InChI=1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1
• InChIKey: UQTZMGFTRHFAAM-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
• IUPAC Traditional name: iodotyrosine; 3-iodo-tyrosine
• Synonyms: 3-Iodotyrosine; (S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acid; 3-Iodo-Tyrosine; 3-Monoiodo-L-tyrosine; 3-IODO-L-TYROSINE; S(-)-3-Iodo-4-hydroxy-phenylamine; 3-Iodo-L-tyrosine; 3-Iodo-4-hydroxyphenylalanine; 3-Iodo-L-tyrosine; 3-Iodotyrosine; 4-Hydroxy-3-iodophenylalanine; MIT; NSC 210787

Database IDs

• CAS Number: 70-78-0
• EC Number: 200-744-8
• MDL Number: MFCD00002608
• Beilstein Number: 2941266
• PubChem SID: 160964988; 24278154; 46507766
• PubChem CID: 6272; 439744
• CHEBI ID: 27847
• CHEMBL: 479789
• Chemspider ID: 388804
• DrugBank ID: DB01758
• Wikipedia Title: 3-Iodotyrosine

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.9928461
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.5602037
• LogD (pH = 7.4): -0.6071167
• Log P: -0.55979866
• Molar Refractivity: 60.4597 cm^3
• Polarizability: 23.81539 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.51
• LOG S: -2.52
• Solubility (Water): 9.37e-01 g/l

PROPERTIES

Physical Property

• Solubility: Dilute Aqeous Acid; Dilute Aqeous Base; dilute aqueous acid: soluble
• Apperance: Off-White Solid
• Melting Point: >180°C (dec.); 204-208 °C (dec.); 210 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -3.1±0.3°, c = 2% in 0.1 M HCl

Safety Information

• Storage Condition: 0°C; 0°C, Desiccate; -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

Pharmacology Properties

• Gene Information: human ... TH(7054)

Product Information

• Purity: ~95%; ~97%; ≥99.0% (HPLC); 95+%; 99%
• Impurities: ~5% tyrosine
• Linear Formula: IC6H3-4-(OH)CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02155069

(3-Monoiodo-L-tyrosine) Crystalline Purity: ~97% May contain up to 3% tyrosine.

MP Biomedicals - 02102367

Crystalline
Purity: ~95%
May contain up to 5% L-tyrosine

MP Biomedicals - 02153684

Purity: 99%

DrugBank - DB01758

Drug information: experimental

Sigma Aldrich - I8250

Biochem/physiol Actions
Tyrosine hydroxylase inhibitor.
包装
1, 5, 25 g in poly bottle

Sigma Aldrich - 58120

Biochem/physiol Actions
Tyrosine hydroxylase inhibitor.
Other Notes
Inhibitor (Ki ~ 500 nM) of tyrosine hydroxylase1,2

Toronto Research Chemicals - I728250

A novel flavoprotein responsible for iodide salvage in thyroid glands. A tyrosine hydroxylase inhibitor.

REFERENCES

• Fitzpatrick, P.F., et al.: Biochemistry, 30, 3658 (1991)
• Harsing, L.G., et al.: Neuroscience, 77, 419 (1991)
• Haynes, C., et al.: J. Biol. Chem., 277, 11513 (1991)