AFCDB: L-Lysine (FDB000474)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:35 UTC

Update date

2019-11-26 02:54:51 UTC

Primary ID

FDB000474

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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 is a very strong basic compound (based on its pKa). L-Lysine exists in all living species, ranging from bacteria to humans. L-Lysine is an odorless tasting compound. L-Lysine is found, on average, in the highest concentration within a few different foods, such as beluga whales, milk (cow), and caseins and in a lower concentration in avocado, sapodilla, and gadus (common cod). L-Lysine has also been detected, but not quantified in, several different foods, such as gins, half-highbush blueberries, lards, ohelo berries, and ucuhuba. This could make L-lysine a potential biomarker for the consumption of these foods. L-Lysine is a potentially toxic compound. L-Lysine, with regard to humans, has been found to be associated with several diseases such as pyruvate carboxylase deficiency, frontotemporal dementia, alzheimer's disease, and supragingival calculus; L-lysine has also been linked to the inborn metabolic disorder carbamoyl phosphate synthetase deficiency.

CAS Number

56-87-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	105 g/L	ALOGPS
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H14N2O2

IUPAC name

(2S)-2,6-diaminohexanoic acid

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

Isomeric SMILES

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

Average Molecular Weight

146.1876

Monoisotopic Molecular Weight

146.105527702

Classification

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 )

Ontology

Leukemia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

All tissues

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Lysinuric protein intolerance

Role

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Anticonvulsant

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 49.30%; H 9.65%; N 19.16%; O 21.89%	DFC
Melting Point	Mp 224-225 dec. (darkens at 210°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	1000 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-3.05	HANSCH,C ET AL. (1995)
Experimental pKa	pKa3 10.54 (25°, 0.1M NaClO4)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +37.9 (5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Lysine, 3 TMS, GC-MS Spectrum	splash10-00di-3910000000-98c565675de67aa87900	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-0ab9-1910000000-87ef8534f592041f50f2	Spectrum
GC-MS	L-Lysine, 4 TMS, GC-MS Spectrum	splash10-0a4i-1921000000-84f7815b0f650fa17444	Spectrum
GC-MS	L-Lysine, 3 TMS, GC-MS Spectrum	splash10-001i-9600000000-823408dba509cb204acf	Spectrum
GC-MS	L-Lysine, 3 TMS, GC-MS Spectrum	splash10-00di-3910000000-4f5578af5e7d8b6c49f7	Spectrum
GC-MS	L-Lysine, 4 TMS, GC-MS Spectrum	splash10-0adi-1921000000-4e56d95e623e792f9e6b	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-00di-0921000000-eeb49e57bc1a75193058	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-0ab9-0921000000-ebb902be0f3754225b2f	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-00di-3910000000-98c565675de67aa87900	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-0ab9-1910000000-87ef8534f592041f50f2	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-0fdk-3923000000-15b84c2649c1b0455de1	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-0a4i-1921000000-84f7815b0f650fa17444	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-001i-9600000000-823408dba509cb204acf	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-00di-3910000000-4f5578af5e7d8b6c49f7	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-0adi-1921000000-4e56d95e623e792f9e6b	Spectrum
GC-MS	L-Lysine, non-derivatized, GC-MS Spectrum	splash10-0abi-1900000000-9ad174122e4d6e003eb8	Spectrum
Predicted GC-MS	L-Lysine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0089-9100000000-974cc55c9130ed5213eb	Spectrum
Predicted GC-MS	L-Lysine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ue9-9700000000-57b24ae819b6ec26bfd2	Spectrum
Predicted GC-MS	L-Lysine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Lysine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Lysine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Lysine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Lysine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Lysine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-003r-8900000000-470a0beb4f338ed89bca	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-74e9193d9d33c2509bfa	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-9000000000-822c4e78250fffa56e39	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-04f9a62a77fb5a37ca22	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-9000000000-035035ecfa084671479b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-5bb15839f86f4fca0d0b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-6c8ef03aa83eb1cab35b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-01ot-0910000000-c182a7dcdbc260666978	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4j-0900000000-6c5f378cef2f14204e15	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-41e1a6499097748934b0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0390000000-7270a0b85b9e3f9f6373	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-a997e809874357908880	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-2900000000-f64110414f82c93e1fe8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014m-9200000000-33a38e6370811c5ddc82	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-3a8b0b6e62f5c66d3720	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-d5167570d11d77fd541e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0900000000-a46231bd529176101129	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9200000000-f8b9f01b2a9886c51df9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-ace0361476d939043e98	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-5b06b6e9dcf9faf8e89c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-053r-9000000000-2894ef6d7f72ea71688e	2012-08-31	View Spectrum
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
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9300000000-f81193f6b50235ec8147	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9300000000-8931d2193adab166d5e4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-0900000000-b4825cc64fcb830c6967	2012-08-31	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB03252

HMDB ID

HMDB00182

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1107871

SuperScent ID

Not Available

Wikipedia ID

Lysine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti alkalotic			DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
essential			DUKE
hypoarginanemic			DUKE

Enzymes

Name	Gene Name	UniProt ID
Aminoadipate-semialdehyde synthase	AASS	A4D0W4
Biotinidase	BTD	P43251
Lysine--tRNA ligase	KARS	Q15046
Lysine-specific demethylase 2A	KDM2A	Q9Y2K7
Lysine-specific demethylase 2B	KDM2B	Q8NHM5

Pathways

Name	SMPDB Link	KEGG Link
Biotin Metabolism	SMP00066	map00780
Carnitine Synthesis	SMP00465	Not Available
Lysine Degradation	SMP00037	map00310
Transcription/Translation	SMP00019	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-Lysine (FDB000474)

Structure for FDB000474 (L-Lysine)