(2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid

• ChemBase ID: 74848
• Molecular Formular: C6H13NO3
• Molecular Mass: 147.17232
• Monoisotopic Mass: 147.08954328
• SMILES: CC(O)[C@H](C)[C@H](N)C(=O)O
• Canonical SMILES: CC([C@@H]([C@@H](C(=O)O)N)C)O
• InChI: InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4?,5-/m0/s1
• InChIKey: OSCCDBFHNMXNME-DSDZBIDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid
• IUPAC Traditional name: (2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid
• Synonyms: 4-Hydroxy-L-isoleucine; (2S,3R,4S)-2-Amino-4-hydroxy-3-methylpentanoic acid; 4-HYDROXYISOLEUCINE; HIL; (4S)-4-Hydroxy-L-isoleucine; (2S,3R)-2-Amino-4-hydroxy-3-methylpentanoic acid; 4-Hydroxy-L-isoleucine

Database IDs

• CAS Number: 55399-93-4; 781658-23-9
• MDL Number: MFCD06799350
• Beilstein Number: 4128096
• PubChem SID: 162039766
• PubChem CID: 2773624

CALCULATED PROPERTIES

• Acid pKa: 2.4603202
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.9314756
• LogD (pH = 7.4): -2.9373093
• Log P: -2.9314218
• Molar Refractivity: 35.7416 cm^3
• Polarizability: 14.5027485 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 147 °C; 296.6 °F
• Optical Rotation: [α]/D +31.0±1.5°, c = 1 in H2O; [α]/D +34.0±2.0°, c = 1 in H2O

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC)
• Biological Source: from fenugreek seed
• Empirical Formula (Hill Notation): C6H13NO3

DETAILS

Sigma Aldrich - 50118

Biochem/physiol Actions
(4S)-4-Hydroxy-L-isoleucine (HIL) is a non-proteinogenic α amino acid produced by the activity of bacterial isoleucine dioxygenase(s). (2S,3R,4S)-HIL is being studied to understand its insulinotropic (anti-diabetic) and anti-obesity effects.
4-Hydroxyisoleucine (HIL) from fenugreek (Trigonella foenum-graecum) seeds is a potential insulinotropic (anti-diabetic) and anti-obesity amino acid. HIL stimulates glucose-dependent insulin secretion from pancreatic cells. HIL activates insulin receptor substrate-associated phosphoinositide 3 (PI3) kinase activity. HIL reduces plasma levels of triglycerides, free fatty acids and cholesterol.

Sigma Aldrich - 49549

Biochem/physiol Actions
A peculiar amino acid extracted from fenugreek seeds and never found in mammalian tissues, exhibits interesting insulinotropic activity; effects on insulin secretion1, plant-derived treatment for metabolic syndrome2.