2-amino-3-hydroxypentanoic acid

• ChemBase ID: 155152
• Molecular Formular: C5H11NO3
• Molecular Mass: 133.14574
• Monoisotopic Mass: 133.07389322
• SMILES: CCC(C(C(=O)O)N)O
• Canonical SMILES: CCC(C(C(=O)O)N)O
• InChI: InChI=1S/C5H11NO3/c1-2-3(7)4(6)5(8)9/h3-4,7H,2,6H2,1H3,(H,8,9)
• InChIKey: LGVJIYCMHMKTPB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-hydroxypentanoic acid
• IUPAC Traditional name: 2-amino-3-hydroxypentanoic acid
• Synonyms: α-Amino-β-hydroxyvaleric acid; 2-Amino-3-hydroxypentanoic acid; 3-Hydroxy-2-aminopentanoic acid; DL-β-Hydroxynorvaline; HNV; DL-3-Hydroxynorvaline

Database IDs

• CAS Number: 2280-42-4
• MDL Number: MFCD00010516
• Beilstein Number: 1722350
• PubChem SID: 24895609; 162249290
• PubChem CID: 65097

CALCULATED PROPERTIES

• Acid pKa: 2.3380196
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.9479287
• LogD (pH = 7.4): -2.9578698
• Log P: -2.9480433
• Molar Refractivity: 30.9838 cm^3
• Polarizability: 12.682326 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC); ≥98.0% (NT)
• Empirical Formula (Hill Notation): C5H11NO3

DETAILS

Sigma Aldrich - H4002

Biochem/physiol Actions
3-Hydroxynorvaline (HNV) is a microbial, α amino acid threonine analogue which has antiviral activity (herpes virus) and is toxic to mammalian cells (embryotoxic and teratogenic) presumably via incorporation into proteins. 3-Hydroxynorvaline may be used as an unnatural amino acid to study the fidelity of protein translation at the level of acyl-tRNA editing. 3-Hydroxynorvaline may also be used to study enzymes and molecules involved in threonine metabolism.

Sigma Aldrich - 56058

Other Notes
Effect of amino acid analogs on the processing of the pancreatic polypeptide precursor in primary cell cultures1