L-lysine (CHEBI:18019)

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CHEBI:18019 - L-lysine

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ChEBI Name	L-lysine

ChEBI ID	CHEBI:18019

ChEBI ASCII Name	L-lysine

Definition	An L-α-amino acid; the L-isomer of lysine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43950, CHEBI:6264, CHEBI:13135, CHEBI:21351

Supplier Information	ChemicalBook:CB4492106, eMolecules:524855, ZINC000001532522

Download	Molfile XML SDF

more structures >>

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Marvin 07280814463D

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Marvin 07280814463D

25 24 0 0 0 0 999 V2000

-0.1131 2.8105 0.1980 N 0 0 0 0 0 0 0 0 0 0 0 0

0.7363 1.6461 0.4840 C 0 0 2 0 0 0 0 0 0 0 0 0

2.1285 1.9012 -0.0320 C 0 0 0 0 0 0 0 0 0 0 0 0

2.3152 2.7450 -0.8760 O 0 0 0 0 0 0 0 0 0 0 0 0

0.1556 0.4101 -0.2060 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2071 0.0782 0.4070 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.7886 -1.1584 -0.2830 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.1500 -1.4906 0.3290 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.7083 -2.6782 -0.3320 N 0 3 0 0 0 0 0 0 0 0 0 0

3.1625 1.1898 0.4460 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.1172 2.9267 -0.8040 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0519 2.5570 0.4640 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7727 1.4791 1.5600 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0563 1.3538 0.1150 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0366 0.6098 -1.2700 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8310 -0.4344 -0.0680 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0875 -0.1223 1.4710 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8833 0.9220 0.2690 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9076 -0.9587 -1.3480 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1124 -2.0023 -0.1450 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0317 -1.6908 1.3940 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8262 -0.6467 0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8184 -2.4919 -1.3180 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0827 -3.4588 -0.2050 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.6068 -2.8973 0.0710 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 11 1 0 0 0 0

1 12 1 0 0 0 0

2 3 1 0 0 0 0

2 5 1 0 0 0 0

2 13 1 0 0 0 0

3 4 2 0 0 0 0

3 10 1 0 0 0 0

5 6 1 0 0 0 0

5 15 1 0 0 0 0

5 16 1 0 0 0 0

6 7 1 0 0 0 0

6 17 1 0 0 0 0

6 18 1 0 0 0 0

7 8 1 0 0 0 0

7 19 1 0 0 0 0

7 20 1 0 0 0 0

8 9 1 0 0 0 0

8 21 1 0 0 0 0

8 22 1 0 0 0 0

9 23 1 0 0 0 0

9 24 1 0 0 0 0

9 25 1 0 0 0 0

10 14 1 0 0 0 0

M CHG 1 9 1

M END): 16 ms

reading 25 atoms

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Wikipedia	License
Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. Lysine contains an α-amino group (which is in the protonated −NH+3 form when the lysine is dissolved in water at physiological pH), an α-carboxylic acid group (which is in the deprotonated −COO− form when the lysine is dissolved in water at physiological pH), and a side chain (CH2)4NH2 (which is partially protonated when the lysine is dissolved in water at physiological pH), and so it is classified as a basic, charged (in water at physiological pH), aliphatic amino acid. It is encoded by the codons AAA and AAG. Like almost all other amino acids, the α-carbon is chiral and lysine may refer to either enantiomer or a racemic mixture of both. For the purpose of this article, lysine will refer to the biologically active enantiomer L-lysine, where the α-carbon is in the S configuration. The human body cannot synthesize lysine. It is essential in humans and must therefore be obtained from the diet. In organisms that synthesise lysine, two main biosynthetic pathways exist, the diaminopimelate and α-aminoadipate pathways, which employ distinct enzymes and substrates and are found in diverse organisms. Lysine catabolism occurs through one of several pathways, the most common of which is the saccharopine pathway. Lysine plays several roles in humans, most importantly proteinogenesis, but also in the crosslinking of collagen polypeptides, uptake of essential mineral nutrients, and in the production of carnitine, which is key in fatty acid metabolism. Lysine is also often involved in histone modifications, and thus, impacts the epigenome. The ε-amino group often participates in hydrogen bonding and as a general base in catalysis. The ε-ammonium group (−NH+3) is attached to the fourth carbon from the α-carbon, which is attached to the carboxyl (−COOH) group. Due to its importance in several biological processes, a lack of lysine can lead to several disease states including defective connective tissues, impaired fatty acid metabolism, anaemia, and systemic protein-energy deficiency. In contrast, an overabundance of lysine, caused by ineffective catabolism, can cause severe neurological disorders. Lysine was first isolated by the German biological chemist Ferdinand Heinrich Edmund Drechsel in 1889 from hydrolysis of the protein casein, and thus named it Lysin, from Greek λύσις (lysis) 'loosening'. In 1902, the German chemists Emil Fischer and Fritz Weigert determined lysine's chemical structur e by synthesizing it. The one-letter symbol K was assigned to lysine for being alphabetically nearest, with L being assigned to the structurally simpler leucine, and M to methionine.
Read full article at Wikipedia

Formula

C6H14N2O2

Net Charge

Average Mass

146.18764

Monoisotopic Mass

146.10553

InChI

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

InChIKey

KDXKERNSBIXSRK-YFKPBYRVSA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. (via lysine )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. anticonvulsant A drug used to prevent seizures or reduce their severity.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-lysine (CHEBI:18019) has role Escherichia coli metabolite (CHEBI:76971) L-lysine (CHEBI:18019) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-lysine (CHEBI:18019) has role algal metabolite (CHEBI:84735) L-lysine (CHEBI:18019) has role anticonvulsant (CHEBI:35623) L-lysine (CHEBI:18019) has role human metabolite (CHEBI:77746) L-lysine (CHEBI:18019) has role micronutrient (CHEBI:27027) L-lysine (CHEBI:18019) has role mouse metabolite (CHEBI:75771) L-lysine (CHEBI:18019) has role nutraceutical (CHEBI:50733) L-lysine (CHEBI:18019) has role plant metabolite (CHEBI:76924) L-lysine (CHEBI:18019) is a L-α-amino acid (CHEBI:15705) L-lysine (CHEBI:18019) is a aspartate family amino acid (CHEBI:22658) L-lysine (CHEBI:18019) is a lysine (CHEBI:25094) L-lysine (CHEBI:18019) is a proteinogenic amino acid (CHEBI:83813) L-lysine (CHEBI:18019) is conjugate acid of L-lysinate (CHEBI:32550) L-lysine (CHEBI:18019) is conjugate base of L-lysinium(1+) (CHEBI:32551) L-lysine (CHEBI:18019) is enantiomer of D-lysine (CHEBI:16855) L-lysine (CHEBI:18019) is tautomer of L-lysine zwitterion (CHEBI:133538) L-lysine (CHEBI:18019) is tautomer of L-Lysine zwitterion (CHEBI:194466)

Incoming	p-Ts-L-Lys-Me (CHEBI:45847) has functional parent L-lysine (CHEBI:18019) L-Lys-D-Asp (CHEBI:144741) has functional parent L-lysine (CHEBI:18019) L-Lys-D-Glu (CHEBI:144743) has functional parent L-lysine (CHEBI:18019) L-lysine derivative (CHEBI:25095) has functional parent L-lysine (CHEBI:18019) L-lysyl-L-amino acid (CHEBI:134263) has functional parent L-lysine (CHEBI:18019) Arg-Lys-Cys-Gly (CHEBI:73401) has functional parent L-lysine (CHEBI:18019) Asn-Lys-His-His (CHEBI:176852) has functional parent L-lysine (CHEBI:18019) Asp-Lys (CHEBI:73829) has functional parent L-lysine (CHEBI:18019) Asp-Lys-Ile (CHEBI:138791) has functional parent L-lysine (CHEBI:18019) desmosine (CHEBI:37628) has functional parent L-lysine (CHEBI:18019) Glu-Glu-Lys (CHEBI:156360) has functional parent L-lysine (CHEBI:18019) Glu-Lys (CHEBI:73521) has functional parent L-lysine (CHEBI:18019) Glu-Lys-Trp-Ala (CHEBI:73487) has functional parent L-lysine (CHEBI:18019) Ile-Lys (CHEBI:141440) has functional parent L-lysine (CHEBI:18019) Leu-Lys (CHEBI:73583) has functional parent L-lysine (CHEBI:18019) Leu-Lys-Asp (CHEBI:138514) has functional parent L-lysine (CHEBI:18019) Lys-Ala (CHEBI:61872) has functional parent L-lysine (CHEBI:18019) Lys-Asp (CHEBI:73601) has functional parent L-lysine (CHEBI:18019) Lys-Asp-Tyr (CHEBI:73598) has functional parent L-lysine (CHEBI:18019) Lys-Gln (CHEBI:73600) has functional parent L-lysine (CHEBI:18019) Lys-Glu-Glu (CHEBI:144461) has functional parent L-lysine (CHEBI:18019) Lys-Glu-Thr (CHEBI:144459) has functional parent L-lysine (CHEBI:18019) Lys-Gly (CHEBI:73604) has functional parent L-lysine (CHEBI:18019) Lys-Leu-Ser (CHEBI:156358) has functional parent L-lysine (CHEBI:18019) Lys-Lys-Leu (CHEBI:156355) has functional parent L-lysine (CHEBI:18019) Lys-Met-Met-Met (CHEBI:73595) has functional parent L-lysine (CHEBI:18019) Lys-Phe (CHEBI:73605) has functional parent L-lysine (CHEBI:18019) Lys-Ser-Trp (CHEBI:144474) has functional parent L-lysine (CHEBI:18019) Lys-Thr (CHEBI:73606) has functional parent L-lysine (CHEBI:18019) Lys-Thr-Pro-Pro (CHEBI:73596) has functional parent L-lysine (CHEBI:18019) Lys-Thr-Trp-Tyr (CHEBI:73597) has functional parent L-lysine (CHEBI:18019) Lys-Tyr (CHEBI:73608) has functional parent L-lysine (CHEBI:18019) Lys-Tyr-Glu (CHEBI:140742) has functional parent L-lysine (CHEBI:18019) Lys-Val (CHEBI:73607) has functional parent L-lysine (CHEBI:18019) Phe-Lys (CHEBI:141443) has functional parent L-lysine (CHEBI:18019) Ser-Asp-Lys (CHEBI:162959) has functional parent L-lysine (CHEBI:18019) Ser-Asp-Lys-Pro (CHEBI:191177) has functional parent L-lysine (CHEBI:18019) Ser-Lys (CHEBI:144702) has functional parent L-lysine (CHEBI:18019) Ser-Trp-Lys (CHEBI:144904) has functional parent L-lysine (CHEBI:18019) Thr-Lys (CHEBI:157893) has functional parent L-lysine (CHEBI:18019) L-lysine hydrochloride (CHEBI:53633) has part L-lysine (CHEBI:18019) royal jelly (CHEBI:78665) has part L-lysine (CHEBI:18019) L-lysinium(1+) (CHEBI:32551) is conjugate acid of L-lysine (CHEBI:18019) L-lysinate (CHEBI:32550) is conjugate base of L-lysine (CHEBI:18019) D-lysine (CHEBI:16855) is enantiomer of L-lysine (CHEBI:18019) N²-L-lysino group (CHEBI:32554) is substituent group from L-lysine (CHEBI:18019) N⁶-L-lysino group (CHEBI:32555) is substituent group from L-lysine (CHEBI:18019) L-lysine residue (CHEBI:29967) is substituent group from L-lysine (CHEBI:18019) L-lysyl group (CHEBI:32553) is substituent group from L-lysine (CHEBI:18019) L-lysine zwitterion (CHEBI:133538) is tautomer of L-lysine (CHEBI:18019) L-Lysine zwitterion (CHEBI:194466) is tautomer of L-lysine (CHEBI:18019)

IUPAC Names

(2S)-2,6-diaminohexanoic acid

L-lysine

INNs	Sources
lysina	WHO MedNet
lysine	WHO MedNet
lysine	WHO MedNet
lysinum	WHO MedNet

Synonyms	Sources
(S)-2,6-diaminohexanoic acid	NIST Chemistry WebBook
(S)-α,ε-diaminocaproic acid	NIST Chemistry WebBook
(S)-lysine	NIST Chemistry WebBook
6-ammonio-L-norleucine	PDBeChem
K	NIST Chemistry WebBook
L-2,6-Diaminocaproic acid	HMDB
L-Lysin	ChEBI
L-Lysine	KEGG COMPOUND
Lys	NIST Chemistry WebBook
Lysine acid	KEGG COMPOUND

Manual Xrefs	Databases
1622	DrugCentral
C00001378	KNApSAcK
C00047	KEGG COMPOUND
D02304	KEGG DRUG
DB00123	DrugBank
ECMDB00182	ECMDB
HMDB0000182	HMDB
LYS	MetaCyc
Lysine	Wikipedia
YMDB00330	YMDB
View more database links

Registry Numbers	Types	Sources
1722531	Reaxys Registry Number	Reaxys
364182	Gmelin Registry Number	Gmelin
56-87-1	CAS Registry Number	KEGG COMPOUND
56-87-1	CAS Registry Number	NIST Chemistry WebBook
56-87-1	CAS Registry Number	ChemIDplus

Citations

Last Modified

08 April 2024

CHEBI:18019 - L-lysine

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