(2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

• ChemBase ID: 133920
• Molecular Formular: C9H11NO5
• Molecular Mass: 213.18734
• Monoisotopic Mass: 213.06372246
• SMILES: c1cc(c(cc1[C@H]([C@@H](C(=O)O)N)O)O)O
• Canonical SMILES: OC(=O)[C@H]([C@@H](c1ccc(c(c1)O)O)O)N
• InChI: InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8+/m0/s1
• InChIKey: QXWYKJLNLSIPIN-JGVFFNPUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
• IUPAC Traditional name: (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
• Synonyms: Droxidopa; L-threo 3,4-Dihydroxyphenylserine; L-DOPS; DL-threo-3,4-Dihydroxyphenylserine; DL-threo-DOPS; DL-threo-β-(3,4-Dihydroxyphenyl)serine

Database IDs

• CAS Number: 23651-95-8; 3916-18-5
• EC Number: 223-480-5
• MDL Number: MFCD00066685; MFCD00799030
• PubChem SID: 162228197; 24893681
• PubChem CID: 92974

CALCULATED PROPERTIES

• Acid pKa: 1.4644188
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.7111156
• LogD (pH = 7.4): -2.7307446
• Log P: -2.7110136
• Molar Refractivity: 50.2856 cm^3
• Polarizability: 19.837856 Å^3
• Polar Surface Area: 124.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble (Solutions should be freshly prepared.); aqueous base: unstable; DMSO: ≥3 mg/mL; ethanol: soluble50 mg/mL (Solutions should be freshly prepared.); H2O: moderately soluble (Solutions should be freshly prepared.)
• Apperance: off-white to yellow-tan powder; white to tan powder

Safety Information

• Storage Condition: desiccated
• RTECS: VT9626000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2; 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC); ≥98% (TLC)
• Empirical Formula (Hill Notation): C9H11NO5

DETAILS

Sigma Aldrich - D2384

Biochem/physiol Actions
Amino acid precursor of noradrenaline (NA); elevates brain NA concentrations.
Quality
May contain variable amounts of erythro isomer.

Sigma Aldrich - D9446

Biochem/physiol Actions
L-DOPS is a norepinephrine precursor in vivo.