Page last updated: 2024-12-07

n(6)-carboxymethyllysine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

N(6)-carboxymethyllysine: RN given refers to (L)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N(6)-carboxymethyl-L-lysine : An L-lysine derivative with a carboxymethyl substituent at the N(6)-position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID123800
CHEBI ID53014
SCHEMBL ID43621
MeSH IDM0139499

Synonyms (41)

Synonym
ne-carboxymethyl-l-lysine
5746-04-3
necml
CHEBI:53014 ,
n(6)-(carboxymethyl)-l-lysine
n(epsilon)-carboxymethyl-l-lysine
n(6)-carboxymethyllysine
n(6)-carboxymethyl-l-lysine
n(epsilon)-(carboxymethyl)lysine
(2s)-2-amino-6-(carboxymethylamino)hexanoic acid
CML ,
AKOS015969256
unii-70ydx3z2o7
l-lysine, n6-(carboxymethyl)-
70ydx3z2o7 ,
n6-(carboxymethyl)lysine
n6-(carboxymethyl)-l-lysine
EPITOPE ID:150904
nepsilon-(carboxymethyl)lysine
NUXSIDPKKIEIMI-LURJTMIESA-N
SCHEMBL43621
cml, n-epsilon-carboxymethyl-l-lysine
mfcd04114278
n6-carboxymethyllysine
(s)-2-amino-6-(carboxymethylamino)hexanoic acid
n.epsilon.-(carboxymethyl)lysine
(2s)-2-amino-6-[(carboxymethyl)amino]hexanoic acid
n'-(carboxymethyl)lysine
2-amino-6-(carboxymethyk-amino)-hexanoic acid
(2~{s})-2-azanyl-6-(2-hydroxy-2-oxoethylamino)hexanoic acid
(s)-2-amino-6-((carboxymethyl)amino)hexanoic acid
(s)-2-amino-6-((carboxymethyl)amino)hexanoicacid
DTXSID80904133
n?-(1-carboxymethyl)-l-lysine
n epsilon -(1-carboxymethyl)-l-lysine
cml - carboxymethyl lysine
nepsilon-(1-carboxymethyl)-l-lysine
CS-0331741
n?-?(1-carboxymethyl)-l-?lysine
nsc-824653
nsc824653

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The estimated LD50 of CML was >5000 mg/kg."( Toxicological evaluation of advanced glycation end product Nε-(carboxymethyl)lysine: Acute and subacute oral toxicity studies.
Gong, Z; Liu, G; Liu, X; Qiao, X; Wu, Y; Xiao, S; Zhang, R; Zheng, L, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
"During processing of pet food, the Maillard reaction occurs, which reduces the bioavailability of essential amino acids such as lysine and results in the formation of advanced Maillard reaction products (MRPs)."( Quantitation of Maillard reaction products in commercially available pet foods.
Alexander, L; Bosch, G; Hendriks, WH; van der Poel, AF; van Rooijen, C; Wierenga, PA, 2014
)
0.4
" Retrospectively, we studied 37 subjects who had participated in a dietary intervention focused on vitamin D bioavailability from white button mushrooms (WBM)."( A Retrospective Study in Adults with Metabolic Syndrome: Diabetic Risk Factor Response to Daily Consumption of Agaricus bisporus (White Button Mushrooms).
Beelman, RB; Cai, W; Calvo, MS; Goh, BC; Kalaras, MD; Mehrotra, A; Nadkarni, G; Uribarri, J; Wang, L, 2016
)
0.43
" The occurrence of the MR during the digestion process may reduce the bioavailability of essential amino acids and increase the production of MRPs causing health disorders."( In vitro formation of Maillard reaction products during simulated digestion of meal-resembling systems.
Cai, W; Del Castillo, MD; Fernandez-Gomez, B; Martinez-Saez, N; Uribarri, J, 2019
)
0.51
"Nɛ-Carboxymethyl-lysine (CML) is a primary advanced glycation end product that exists in the body and food as free and bound forms with different bioavailability and physiological effects."( Comparison of tissue distribution of free and protein bound Nɛ-carboxymethyllysine after long-term oral administration to mice.
Bai, Y; Chen, Z; Li, J; Li, S; Nie, C; Tu, A; Yuan, X; Zhai, R; Zhang, J; Zhang, M, 2022
)
0.72
" To thoroughly understand the bioavailability of free Nɛ-carboxymethyllysine (CML) and bovine serum albumin (BSA)-CML in vivo after intragastric administration, pharmacokinetics, biodistribution, and excretion of CML in rats were investigated by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS)."( Comparison of pharmacokinetics, biodistribution, and excretion of free and bound Nε-carboxymethyllysine in rats by HPLC-MS/MS.
Bai, Y; Chen, T; Chen, Z; Huang, T; Li, J; Xie, X; Yuan, X; Zhai, R; Zheng, M, 2023
)
0.91

Dosage Studied

ExcerptRelevanceReference
" Twelve db/db mice were given a solution containing a daily dosage of L-arginine of 50 mg/kg body weight orally."( L-arginine reduces glomerular basement membrane collagen N epsilon-carboxymethyllysine in the diabetic db/db mouse.
Höger, H; Lubec, B; Lubec, G; Szalay, S; Weninger, M; Xi, Z, 1992
)
0.28
" The dose-response curve for ET-1 was shifted to the left in the diabetics, so that at some lower doses of ET-1 the vasoconstriction was greater than in the controls."( Diabetes-associated changes and role of N epsilon-(carboxymethyl)lysine in big ET-1-induced coronary vasoconstriction.
Kamata, K; Kobayashi, T; Matsumoto, T; Ozawa, Y; Taguchi, K, 2010
)
0.36
" In subacute toxicity test, CML was dosed at 200, 500 and 1000 mg/kg in both genders for 28 days."( Toxicological evaluation of advanced glycation end product Nε-(carboxymethyl)lysine: Acute and subacute oral toxicity studies.
Gong, Z; Liu, G; Liu, X; Qiao, X; Wu, Y; Xiao, S; Zhang, R; Zheng, L, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antigenAny substance that stimulates an immune response in the body, such as through antibody production or by presentation to a T-cell receptor after binding to a major histocompability complex (MHC).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
L-lysine derivativeA proteinogenic amino acid derivative resulting from reaction of L-lysine at the amino group or the carboxy group, or from the replacement of any hydrogen of L-lysine by a heteroatom.
non-proteinogenic L-alpha-amino acidAny L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (777)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (0.39)18.7374
1990's91 (11.71)18.2507
2000's290 (37.32)29.6817
2010's318 (40.93)24.3611
2020's75 (9.65)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.77

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index9.77 (24.57)
Research Supply Index6.74 (2.92)
Research Growth Index6.52 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.77)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials44 (5.48%)5.53%
Reviews25 (3.11%)6.00%
Case Studies2 (0.25%)4.05%
Observational8 (1.00%)0.25%
Other724 (90.16%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]