Bovine Metabolome Database: Showing metabocard for L-Isoleucine (BMDB0000172)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:30 UTC

Update Date

2020-06-04 22:12:11 UTC

BMDB ID

BMDB0000172

Secondary Accession Numbers

BMDB00172

Metabolite Identification

Common Name

L-Isoleucine

Description

L-Isoleucine, also known as I, 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. Thus, L-isoleucine is considered to be a fatty acid lipid molecule. L-Isoleucine exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. L-Isoleucine exists in all living species, ranging from bacteria to humans. L-Isoleucine is a potentially toxic compound.

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 Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

IUPAC Name

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

Traditional Name

L-isoleucine

CAS Registry Number

73-32-5

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 )

Ontology

Status

Detected and Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	285.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	35 mg/mL	Human Metabolome Project
LogP	-1.7	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0a4i-0930000000-e78f845bb2a8d4736476	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0a4i-0910000000-de9162d149073d0e2a37	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0a4i-0920000000-599e61f8ccdb6525c7a9	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0910000000-742e44c426c0d6c2a9ac	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-05fr-8910000000-dbb33e0f02ac2ca5fedd	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0920000000-37690f426455ac41e2c2	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-e78f845bb2a8d4736476	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-de9162d149073d0e2a37	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0920000000-599e61f8ccdb6525c7a9	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-742e44c426c0d6c2a9ac	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0udi-2392000000-74cca1eb265b8e3d7f43	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fr-8910000000-dbb33e0f02ac2ca5fedd	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9100000000-27891dff695c5db53796	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-43ec1890f6dbd6aea657	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9100000000-40bc9ef43da5f18be883	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9200000000-ae8694c0f3e4dcc608f9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9300000000-8a23b3e62231eb65f80f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ko-9000000000-ac7e71578d7e1d0e8ce9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-2586d4a089921dd977ed	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-5b11521ff6a631376d2b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-3c352f229e4067fcd489	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-8a7ef48fc0c1b6f845c2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0920000000-2e11aa1c7a5defc386db	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-b63ac9cf06eda4c54a81	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-e5b0c8c6b09f541d6dbf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-d89d16d5c2242e44ec63	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-5de583142c7bdb381c8f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-8c75bde35c4a4073ee65	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-233a9862f616afea2d17	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-1900000000-375f35065b82b13e6d6e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00dl-9000000000-d0d4a9f90fe2aca74483	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-0018f47571feaf232ff8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001r-7900000000-278dc67396114be331ba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9000000000-e26c042aa6231eeca071	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014r-9000000000-b6c1752fd3fbccb3d1c5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-05mo-9000000000-0569c3162621252ed0a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-052f-9000000000-3d52b5d56d3fab45276e	View in MoNA
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	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9500000000-00268b2694cde281641b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-4014793e17e0290790a4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-eb9a97a14461e524e76e	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-004r-9000000000-34d4d4cb7042da231eb4	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 22.5 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

All Tissues
Blood
Colostrum
Liver
Longissimus Thoracis Muscle
Mammary Gland
Milk
Muscle
Placenta
Prostate Tissue
Ruminal Fluid
Semen
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Valine, Leucine, and Isoleucine Degradation		Not Available
Protein Synthesis: Isoleucine		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22370585	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25372282	details
Blood	Detected and Quantified	71.5 uM	Not Specified	Not Specified	Normal	PMID: 17197001	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25913299	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24440255	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Jiyuan Li, Everes...	details
Blood	Detected and Quantified	76-101 uM	Not Specified	Not Specified	Normal	PMID: 11204708	details
Blood	Detected and Quantified	72.05 uM	Not Specified	Both	Normal	PMID: 9374324	details
Blood	Detected and Quantified	101-122 uM	Not Specified	Not Specified	Normal	PMID: 3535614	details
Blood	Detected and Quantified	63-118 uM	Not Specified	Not Specified	Normal	PMID: 28453535	details
Blood	Detected and Quantified	95-103 uM	Not Specified	Not Specified	Normal	PMID: 28036059	details
Blood	Detected and Quantified	153 +/- 14 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22361340	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected and Quantified	178 +/- 29 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	107 +/- 22 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected and Quantified	5.15 +/- 1.64 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	3 - 14 uM	Not Specified	Not Specified	Normal	PMID: 20338431	details
Milk	Detected and Quantified	2 - 13 uM	Not Specified	Not Specified	Normal	PMID: 20338431	details
Milk	Detected and Quantified	3.9 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4.5 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4.5 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4.8 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	15247.0518 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	15247.0518 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	15247.0518 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	15247.0518 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	15247.0518 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	15247.0518 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	15247.0518 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	4.33 +/- 1.74 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	4.4 +/- 0.5 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4.2 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	3.9 +/- 0.6 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4.7 +/- 0.7 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4.20 +/- 1.53 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23497994	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23182357	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25087032	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22361340	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Muscle	Detected and Quantified	215.92 +/- 14.82 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	43-231 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	46.75 +/- 3.37 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	387770 +/- 50250 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	2360 +/- 380 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	640 +/- 70 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	970 +/- 120 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	370 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 26437054	details
Muscle	Detected and Quantified	72.44 +/- 10.27 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	85.7 +/- 14.97 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	5-11 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 28465593	details
Muscle	Detected and Quantified	160-588 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 30744349	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	151.8 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	266.9 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	182.9 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	173.8 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	123-1210 uM	Not Specified	Not Specified	Normal	PMID: 22706048	details
Ruminal Fluid	Detected and Quantified	137 +/- 40 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	235 +/- 62 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	183 +/- 74 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	147 +/- 42 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	147 +/- 42 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	48-144 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24617926	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Hanne Christine B...	details
Ruminal Fluid	Detected and Quantified	124 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	222 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	148 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	144 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22706048	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22706048	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22706048	details
Ruminal Fluid	Detected and Quantified	556 +/- 127 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	173.85 +/- 19.76 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 5096119	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29634739	details
Semimembranosus Muscle	Detected and Quantified	116 +/- 23 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	30 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 5096119	details
Testis	Detected and Quantified	79 +/- 14 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Treated with growth-promoting hormones	PMID: 22370585	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	All Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	High dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Low dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Sub/clinical ketosis	PMID: 24070026	details
Blood	Detected and Quantified	76.9 uM	Not Specified	Not Specified	Bovine spongiform encephalopathy negative	PMID: 17197001	details
Blood	Detected and Quantified	82.3 uM	Not Specified	Not Specified	Bovine spongiform encephalopathy positive	PMID: 17197001	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Commercial Product/bacterial growth on ground beef	PMID: 22417363	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Commercial Product/bacterial growth on ground beef	PMID: 22417363	details
Ruminal Fluid	Detected and Quantified	182.86 +/- 71.9 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details

External Links

HMDB ID

HMDB0000172

DrugBank ID

DB00167

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17191

References

Synthesis Reference

Marvel, C. S. L-Isoleucine. Organic Syntheses (1941), 21 60-4.

Material Safety Data Sheet (MSDS)

Not Available

General References

Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

Enzyme Details

1. Branched-chain-amino-acid aminotransferase

General function:: Amino acid transport and metabolism
Specific function:: Not Available
Gene Name:: BCAT1
Uniprot ID:: A4IFQ7
Molecular weight:: 43185.0

Enzyme Details

2. Branched-chain-amino-acid aminotransferase, mitochondrial

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids (By similarity).
Gene Name:: BCAT2
Uniprot ID:: Q5EA40
Molecular weight:: 44648.0

Reactions

L-Isoleucine + Oxoglutaric acid → 3-Methyl-2-oxovaleric acid + L-Glutamic acid	details

Enzyme Details

3. Branched-chain-amino-acid aminotransferase

General function:: Amino acid transport and metabolism
Specific function:: Not Available
Gene Name:: BCAT2
Uniprot ID:: Q0V8J6
Molecular weight:: 44274.0

Enzyme Details

4. Branched-chain-amino-acid aminotransferase

General function:: Amino acid transport and metabolism
Specific function:: Not Available
Gene Name:: BCAT2
Uniprot ID:: Q5E9U7
Molecular weight:: 40447.0

Enzyme Details

5. IARS protein

General function:: Translation, ribosomal structure and biogenesis
Specific function:: Not Available
Gene Name:: IARS1
Uniprot ID:: A7MBC5
Molecular weight:: 144642.0

Reactions

Adenosine triphosphate + L-Isoleucine + tRNA(Ile) → Adenosine monophosphate + Pyrophosphate + L-Isoleucyl-tRNA(Ile)	details

Showing metabocard for L-Isoleucine (BMDB0000172)

Structure for BMDB0000172 (L-Isoleucine)

Enzymes

Reactions

Reactions