ContaminantDB: L-Isoleucine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:35:06 UTC

Update Date

2026-04-17 18:55:30 UTC

Accession Number

CHEM003324

Identification

Common Name

L-Isoleucine

Class

Small Molecule

Description

L-Isoleucine is one of the essential amino acids that cannot be made by the body and is known for its ability to help endurance and assist in the repair and rebuilding of muscle. This amino acid is important to body builders as it helps boost energy and helps the body recover from training. L-Isoleucine is also classified as a branched-chain amino acid (BCAA). It helps promote muscle recovery after exercise. Isoleucine is actually broken down for energy within the muscle tissue. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.

Contaminant Sources

Cosmetic Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Amino Acid, Essential
Animal Toxin
Dietary Supplement
Drug
Food Toxin
Household Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2S,3S)-2-Amino-3-methylpentanoic acid	ChEBI
2-Amino-3-methylvaleric acid	ChEBI
alpha-Amino-beta-methylvaleric acid	ChEBI
I	ChEBI
Ile	ChEBI
ISOLEUCINE	ChEBI
(2S,3S)-2-Amino-3-methylpentanoate	Generator
2-Amino-3-methylvalerate	Generator
a-Amino-b-methylvalerate	Generator
a-Amino-b-methylvaleric acid	Generator
alpha-Amino-beta-methylvalerate	Generator
Α-amino-β-methylvalerate	Generator
Α-amino-β-methylvaleric acid	Generator
(2S,3S)-2-Amino-3-methyl-pentanoate	HMDB
(2S,3S)-2-Amino-3-methyl-pentanoic acid	HMDB
(2S,3S)-a-Amino-b-methyl-N-valerate	HMDB
(2S,3S)-a-Amino-b-methyl-N-valeric acid	HMDB
(2S,3S)-a-Amino-b-methylvalerate	HMDB
(2S,3S)-a-Amino-b-methylvaleric acid	HMDB
(2S,3S)-Alph-amino-beta-methylvalerate	HMDB
(2S,3S)-Alph-amino-beta-methylvaleric acid	HMDB
(2S,3S)-alpha-Amino-beta-merthyl-N-valerate	HMDB
(2S,3S)-alpha-Amino-beta-merthyl-N-valeric acid	HMDB
(2S,3S)-alpha-Amino-beta-merthylvalerate	HMDB
(2S,3S)-alpha-Amino-beta-merthylvaleric acid	HMDB
(2S,3S)-alpha-Amino-beta-methyl-N-valerate	HMDB
(2S,3S)-alpha-Amino-beta-methyl-N-valeric acid	HMDB
(2S,3S)-alpha-Amino-beta-methylvalerate	HMDB
(2S,3S)-alpha-Amino-beta-methylvaleric acid	HMDB
(S)-Isoleucine	HMDB
(S,S)-Isoleucine	HMDB
2-Amino-3-methylpentanoate	HMDB
2-Amino-3-methylpentanoic acid	HMDB
2S,3S-Isoleucine	HMDB
Erythro-L-isoleucine	HMDB
Iso-leucine	HMDB
L-(+)-Isoleucine	HMDB
L-Ile	HMDB
[S-(R,r)]-2-amino-3-methylpentanoate	HMDB
[S-(R,r)]-2-amino-3-methylpentanoic acid	HMDB
Isoleucine, L-isomer	HMDB
Alloisoleucine	HMDB
Isoleucine, L isomer	HMDB
L-Isomer isoleucine	HMDB
2S-Amino-3S-methylpentanoate	HMDB
L-Isoleucine	KEGG

Chemical Formula

C₆H₁₃NO₂

Average Molecular Mass

131.173 g/mol

Monoisotopic Mass

131.095 g/mol

CAS Registry Number

73-32-5

IUPAC Name

(2S,3S)-2-amino-3-methylpentanoic acid

Traditional Name

L-isoleucine

SMILES

CC[C@H](C)[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1

InChI Key

AGPKZVBTJJNPAG-WHFBIAKZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Isoleucine and derivatives

Alternative Parents

Substituents

Isoleucine or derivatives
Alpha-amino acid
L-alpha-amino acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acid
Fatty acyl
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:17191 )
proteinogenic amino acid (CHEBI:17191 )
L-alpha-amino acid (CHEBI:17191 )
isoleucine (CHEBI:17191 )
Common amino acids (C00407 )
Amino fatty acids (LMFA01100047 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

All Tissues
Prostate

Pathways

Name	SMPDB Link	KEGG Link
Transcription/Translation	SMP00019	Not Available
Valine, Leucine and Isoleucine Degradation	SMP00032	map00280
Hartnup Disorder	SMP00189	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	285.5 dec°C
Boiling Point	Not Available
Solubility	3.44E+004 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	114 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.5	ChemAxon
logS	-0.06	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	9.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.09 m³·mol⁻¹	ChemAxon
Polarizability	14.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0a4i-0930000000-e78f845bb2a8d4736476	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0a4i-0910000000-de9162d149073d0e2a37	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0a4i-0920000000-599e61f8ccdb6525c7a9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0910000000-742e44c426c0d6c2a9ac	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-05fr-8910000000-dbb33e0f02ac2ca5fedd	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0920000000-37690f426455ac41e2c2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-e78f845bb2a8d4736476	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-de9162d149073d0e2a37	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0920000000-599e61f8ccdb6525c7a9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-742e44c426c0d6c2a9ac	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0udi-2392000000-74cca1eb265b8e3d7f43	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fr-8910000000-dbb33e0f02ac2ca5fedd	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9100000000-27891dff695c5db53796	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-43ec1890f6dbd6aea657	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9100000000-40bc9ef43da5f18be883	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9200000000-ae8694c0f3e4dcc608f9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9300000000-8a23b3e62231eb65f80f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ko-9000000000-ac7e71578d7e1d0e8ce9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-2586d4a089921dd977ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-5b11521ff6a631376d2b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-3c352f229e4067fcd489	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-8a7ef48fc0c1b6f845c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0920000000-2e11aa1c7a5defc386db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-b63ac9cf06eda4c54a81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-e5b0c8c6b09f541d6dbf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-d89d16d5c2242e44ec63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-5de583142c7bdb381c8f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-8c75bde35c4a4073ee65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-233a9862f616afea2d17	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-1900000000-375f35065b82b13e6d6e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00dl-9000000000-d0d4a9f90fe2aca74483	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-0018f47571feaf232ff8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001r-7900000000-278dc67396114be331ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9000000000-e26c042aa6231eeca071	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014r-9000000000-b6c1752fd3fbccb3d1c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-05mo-9000000000-0569c3162621252ed0a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-052f-9000000000-3d52b5d56d3fab45276e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-001i-0900000000-720554d58264a9cfdb67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9500000000-00268b2694cde281641b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-4014793e17e0290790a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-eb9a97a14461e524e76e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004r-9000000000-34d4d4cb7042da231eb4	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Absorbed from the small intestine by a sodium-dependent active-transport process

Mechanism of Toxicity

(Applies to Valine, Leucine and Isoleucine)
This group of essential amino acids are identified as the branched-chain amino acids, BCAAs. Because this arrangement of carbon atoms cannot be made by humans, these amino acids are an essential element in the diet. The catabolism of all three compounds initiates in muscle and yields NADH and FADH2 which can be utilized for ATP generation. The catabolism of all three of these amino acids uses the same enzymes in the first two steps. The first step in each case is a transamination using a single BCAA aminotransferase, with a-ketoglutarate as amine acceptor. As a result, three different a-keto acids are produced and are oxidized using a common branched-chain a-keto acid dehydrogenase, yielding the three different CoA derivatives. Subsequently the metabolic pathways diverge, producing many intermediates.
The principal product from valine is propionylCoA, the glucogenic precursor of succinyl-CoA. Isoleucine catabolism terminates with production of acetylCoA and propionylCoA; thus isoleucine is both glucogenic and ketogenic. Leucine gives rise to acetylCoA and acetoacetylCoA, and is thus classified as strictly ketogenic.
There are a number of genetic diseases associated with faulty catabolism of the BCAAs. The most common defect is in the branched-chain a-keto acid dehydrogenase. Since there is only one dehydrogenase enzyme for all three amino acids, all three a-keto acids accumulate and are excreted in the urine. The disease is known as Maple syrup urine disease because of the characteristic odor of the urine in afflicted individuals. Mental retardation in these cases is extensive. Unfortunately, since these are essential amino acids, they cannot be heavily restricted in the diet; ultimately, the life of afflicted individuals is short and development is abnormal The main neurological problems are due to poor formation of myelin in the CNS.

Metabolism

Hepatic

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

The branched-chain amino acids may have antihepatic encephalopathy activity in some. They may also have anticatabolic and antitardive dyskinesia activity.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of hypoglycemia

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00167

HMDB ID

HMDB0000172

FooDB ID

FDB012397

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Nelli I. Zhdanova, Tatyana V. Leonova, Ljudmila F. Kozyreva, “Method of producing L-isoleucine using Brevibacterium flavum.” U.S. Patent US4237228, issued February, 1962.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14651987

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16140883

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17299083

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17409434

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22298573

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24284437

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24406630

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24738868

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24831709