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:CB3326778, eMolecules:518114, eMolecules:1844537, ZINC000000388081

Download	Molfile XML SDF

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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): 20 ms

reading 25 atoms

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Wikipedia	License
Ammonium is a modified form of ammonia that has an extra hydrogen atom. It is a positively charged (cationic) molecular ion with the chemical formula NH+4 or [NH4]+. It is formed by the addition of a proton (a hydrogen nucleus) to ammonia (NH3). Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations ([NR4]+), where one or more hydrogen atoms are replaced by organic or other groups (indicated by R). Not only is ammonium a source of nitrogen and a key metabolite for many living organisms, but it is an integral part of the global nitrogen cycle. As such, human impact in recent years could have an effect on the biological communities that depend on it.
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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