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781658-23-9 molecular structure
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(2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid

ChemBase ID: 74848
Molecular Formular: C6H13NO3
Molecular Mass: 147.17232
Monoisotopic Mass: 147.08954328
SMILES and InChIs

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

Cite this record

CBID:74848 http://www.chembase.cn/molecule-74848.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
781658-23-9
55399-93-4
MDL Number
MFCD06799350
Beilstein Number
4128096
PubChem SID
162039766
PubChem CID
2773624

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 2773624 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.4603202  H Acceptors
H Donor LogD (pH = 5.5) -2.9314756 
LogD (pH = 7.4) -2.9373093  Log P -2.9314218 
Molar Refractivity 35.7416 cm3 Polarizability 14.5027485 Å3
Polar Surface Area 83.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Flash Point
147 °C expand Show data source
296.6 °F expand Show data source
Optical Rotation
[α]/D +31.0±1.5°, c = 1 in H2O expand Show data source
[α]/D +34.0±2.0°, c = 1 in H2O expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (TLC) expand Show data source
Biological Source
from fenugreek seed expand Show data source
Empirical Formula (Hill Notation)
C6H13NO3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 50118 external link
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 external link
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.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

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