Milk Composition Database: Showing metabocard for L-Lysine (BMDB0000182)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:37 UTC

Update Date

2020-06-04 22:22:06 UTC

MCDB ID

BMDB0000182

Secondary Accession Numbers

BMDB00182

Metabolite Identification

Common Name

L-Lysine

Description

L-Lysine, also known as (S)-lysine or L-lysin, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Lysine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Lysine exists in all living species, ranging from bacteria to humans. In cattle, L-lysine is involved in the metabolic pathway called the biotin metabolism pathway. L-Lysine is a potentially toxic compound. L-Lysine has been found to be associated with several diseases known as citrullinemia type ii, neonatal-onset, autism, and leukemia; also l-lysine has been linked to several inborn metabolic disorders including histidinemia and fumarase deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2,6-Diaminohexanoic acid	ChEBI
(S)-alpha,epsilon-Diaminocaproic acid	ChEBI
(S)-Lysine	ChEBI
6-Ammonio-L-norleucine	ChEBI
K	ChEBI
L-2,6-Diaminocaproic acid	ChEBI
L-Lysin	ChEBI
Lys	ChEBI
Lysina	ChEBI
Lysine	ChEBI
Lysine acid	ChEBI
Lysinum	ChEBI
2,6-Diaminohexanoic acid	Kegg
(S)-2,6-Diaminohexanoate	Generator
(S)-a,epsilon-Diaminocaproate	Generator
(S)-a,epsilon-Diaminocaproic acid	Generator
(S)-alpha,epsilon-Diaminocaproate	Generator
(S)-Α,epsilon-diaminocaproate	Generator
(S)-Α,epsilon-diaminocaproic acid	Generator
L-2,6-Diaminocaproate	Generator
2,6-Diaminohexanoate	Generator
(+)-S-Lysine	HMDB
(S)-2,6-Diamino-hexanoate	HMDB
(S)-2,6-Diamino-hexanoic acid	HMDB
(S)-a,e-Diaminocaproate	HMDB
(S)-a,e-Diaminocaproic acid	HMDB
6-Amino-aminutrin	HMDB
6-Amino-L-norleucine	HMDB
a-Lysine	HMDB
alpha-Lysine	HMDB
Aminutrin	HMDB
H-Lys-OH	HMDB
L-(+)-Lysine	HMDB
L-2,6-Diainohexanoate	HMDB
L-2,6-Diainohexanoic acid	HMDB
L-Lys	HMDB
Acetate, lysine	HMDB
Enisyl	HMDB
Lysine hydrochloride	HMDB
L Lysine	HMDB
Lysine acetate	HMDB

Chemical Formula

C₆H₁₄N₂O₂

Average Molecular Weight

146.1876

Monoisotopic Molecular Weight

146.105527702

IUPAC Name

(2S)-2,6-diaminohexanoic acid

Traditional Name

L-lysine

CAS Registry Number

56-87-1

SMILES

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

InChI Identifier

InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1

InChI Key

KDXKERNSBIXSRK-YFKPBYRVSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lysine (CHEBI:18019 )
aspartate family amino acid (CHEBI:18019 )
proteinogenic amino acid (CHEBI:18019 )
L-alpha-amino acid (CHEBI:18019 )
Common amino acids (C00047 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	224.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL	Not Available
LogP	-3.05	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-3.8	ALOGPS
logP	-3.2	ChemAxon
logS	-0.14	ALOGPS
pKa (Strongest Acidic)	2.74	ChemAxon
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.81 m³·mol⁻¹	ChemAxon
Polarizability	15.84 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) (3 TMS)	splash10-00di-3910000000-98c565675de67aa87900	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)	splash10-0ab9-1910000000-87ef8534f592041f50f2	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0a4i-1921000000-84f7815b0f650fa17444	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001i-9600000000-823408dba509cb204acf	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-3910000000-4f5578af5e7d8b6c49f7	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0adi-1921000000-4e56d95e623e792f9e6b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-0921000000-eeb49e57bc1a75193058	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-0921000000-ebb902be0f3754225b2f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-3910000000-98c565675de67aa87900	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ab9-1910000000-87ef8534f592041f50f2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0fdk-3923000000-15b84c2649c1b0455de1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-1921000000-84f7815b0f650fa17444	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-9600000000-823408dba509cb204acf	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-3910000000-4f5578af5e7d8b6c49f7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0adi-1921000000-4e56d95e623e792f9e6b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0abi-1900000000-9ad174122e4d6e003eb8	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0089-9100000000-974cc55c9130ed5213eb	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0ue9-9700000000-57b24ae819b6ec26bfd2	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 (TMS_1_3) - 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-003r-8900000000-470a0beb4f338ed89bca	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-74e9193d9d33c2509bfa	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-9000000000-822c4e78250fffa56e39	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-04f9a62a77fb5a37ca22	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-9000000000-035035ecfa084671479b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-5bb15839f86f4fca0d0b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-6c8ef03aa83eb1cab35b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-01ot-0910000000-c182a7dcdbc260666978	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4j-0900000000-6c5f378cef2f14204e15	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-41e1a6499097748934b0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0390000000-7270a0b85b9e3f9f6373	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-a997e809874357908880	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-2900000000-f64110414f82c93e1fe8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014m-9200000000-33a38e6370811c5ddc82	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-3a8b0b6e62f5c66d3720	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-d5167570d11d77fd541e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0900000000-a46231bd529176101129	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9200000000-f8b9f01b2a9886c51df9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-ace0361476d939043e98	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-5b06b6e9dcf9faf8e89c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-053r-9000000000-2894ef6d7f72ea71688e	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	splash10-0002-0900000000-290902f43cf851e8ef5e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9300000000-f81193f6b50235ec8147	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9300000000-8931d2193adab166d5e4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-0900000000-b4825cc64fcb830c6967	2012-08-31	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 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	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	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 but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	7 - 102 uM	PMID: 20338431	details
Detected and Quantified	21205 uM	Fooddata+, T...	details
Detected and Quantified	21205 uM	Fooddata+, T...	details
Detected and Quantified	21205 uM	Fooddata+, T...	details
Detected and Quantified	21205 uM	Fooddata+, T...	details
Detected and Quantified	21205 uM	Fooddata+, T...	details
Detected and Quantified	21205 uM	Fooddata+, T...	details
Detected and Quantified	21205 uM	Fooddata+, T...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	18 +/- 9 uM	PMID: 30994344	details
Detected and Quantified	23 +/- 3 uM	PMID: 30994344	details
Detected and Quantified	24 +/- 5 uM	PMID: 30994344	details
Detected and Quantified	25 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	30 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	21 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	26 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	22 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	27 +/- 24 uM	PMID: 23931703	details

External Links

HMDB ID

HMDB0000182

DrugBank ID

DB00123

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

ChEBI ID

References

Synthesis Reference

Rothstein, Morton. DL-Lysine-6-C14 and DL-a-aminoadipic acid-6-C14. Biochemical Preparations (1961), 8 85-8.

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 ]
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 ]
Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug 23. [PubMed:23931703 ]
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-Lysine (BMDB0000182)

Structure for BMDB0000182 (L-Lysine)