Milk Composition Database: Showing metabocard for L-Isoleucine (BMDB0000172)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:30 UTC

Update Date

2020-06-04 22:12:11 UTC

MCDB 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 )

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	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	Deposition Date	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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0920000000-37690f426455ac41e2c2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-e78f845bb2a8d4736476	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-de9162d149073d0e2a37	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0920000000-599e61f8ccdb6525c7a9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-742e44c426c0d6c2a9ac	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0udi-2392000000-74cca1eb265b8e3d7f43	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fr-8910000000-dbb33e0f02ac2ca5fedd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9100000000-27891dff695c5db53796	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-43ec1890f6dbd6aea657	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9100000000-40bc9ef43da5f18be883	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9200000000-ae8694c0f3e4dcc608f9	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9300000000-8a23b3e62231eb65f80f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ko-9000000000-ac7e71578d7e1d0e8ce9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-2586d4a089921dd977ed	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-5b11521ff6a631376d2b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-3c352f229e4067fcd489	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-8a7ef48fc0c1b6f845c2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0920000000-2e11aa1c7a5defc386db	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-b63ac9cf06eda4c54a81	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-e5b0c8c6b09f541d6dbf	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-d89d16d5c2242e44ec63	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-5de583142c7bdb381c8f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-8c75bde35c4a4073ee65	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-233a9862f616afea2d17	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-1900000000-375f35065b82b13e6d6e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00dl-9000000000-d0d4a9f90fe2aca74483	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-0018f47571feaf232ff8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001r-7900000000-278dc67396114be331ba	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9000000000-e26c042aa6231eeca071	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014r-9000000000-b6c1752fd3fbccb3d1c5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-05mo-9000000000-0569c3162621252ed0a8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-052f-9000000000-3d52b5d56d3fab45276e	2012-08-31	View 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	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9500000000-00268b2694cde281641b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-4014793e17e0290790a4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-eb9a97a14461e524e76e	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004r-9000000000-34d4d4cb7042da231eb4	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.5 MHz, D₂O, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
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	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	3 - 14 uM	PMID: 20338431	details
Detected but not Quantified	Not Applicable	PMID: 23497994	details
Detected but not Quantified	Not Applicable	PMID: 23182357	details
Detected but not Quantified	Not Applicable	PMID: 25087032	details
Detected and Quantified	2 - 13 uM	PMID: 20338431	details
Detected and Quantified	15247 uM	Fooddata+, T...	details
Detected and Quantified	15247 uM	Fooddata+, T...	details
Detected and Quantified	15247 uM	Fooddata+, T...	details
Detected and Quantified	15247 uM	Fooddata+, T...	details
Detected and Quantified	15247 uM	Fooddata+, T...	details
Detected and Quantified	15247 uM	Fooddata+, T...	details
Detected and Quantified	15247 uM	Fooddata+, T...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	4.4 +/- 0.5 uM	PMID: 30994344	details
Detected and Quantified	4.2 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	3.9 +/- 0.6 uM	PMID: 30994344	details
Detected and Quantified	4.7 +/- 0.7 uM	PMID: 30994344	details
Detected and Quantified	3.9 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	4.5 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	4.5 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	4.8 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	4.33 +/- 1.74 uM	PMID: 29642378	details
Detected and Quantified	4.2 +/- 1.53 uM	PMID: 29642378	details
Detected and Quantified	5.2 +/- 1.64 uM	PMID: 29642378	details

External Links

HMDB ID

HMDB0000172

DrugBank ID

DB00167

Phenol Explorer Compound ID

Not Available

FoodDB 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)

Download (PDF)

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]

Showing metabocard for L-Isoleucine (BMDB0000172)

Structure for BMDB0000172 (L-Isoleucine)