4252 N(6)-Carboxymethyllysine N(6)-Carboxymethyllysine is an endogenous organic compound with the formula C8H16N2O4 and an average molecular weight of 204.22 g/mol. It exists as a solid at room temperature. N(6)-Carboxymethyllysine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is an advanced glycation endproduct (AGE) and serves as a uremic toxin. It has been extensively used as a marker for AGEs in food analysis. Its recorded protein target is the organic anion transporter 3 (SLC22A8). 5746-04-3 C8H16N2O4 White powder. Endogenous, Ingestion, Dermal (contact) Uremic toxins such as carboxymethyllysine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869). Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces. No indication of carcinogenicity to humans (not listed by IARC). Naturally produced by the body (endogenous). Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. 2014-08-29T05:52:11Z 2026-04-06T12:30:12Z N(6)-Carboxymethyllysine true NC(CCCCNCC(O)=O)C(O)=O C8H16N2O4 InChI=1S/C8H16N2O4/c9-6(8(13)14)3-1-2-4-10-5-7(11)12/h6,10H,1-5,9H2,(H,11,12)(H,13,14) NUXSIDPKKIEIMI-UHFFFAOYSA-N 204.2236 204.11100701 Endogenous Solid CHEM003158 NS00123889 112.64999999999999 48.668699999999994 21.207122857673014 8 6 4 1.6051481211176375 10.597717437593165 0 0 -2.98 -1.24 1.18e+01 g/l Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues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 ï¾­Þ�������������������� ���€���`�������`�������`�������`�������`�������`�������`�������`�������(�������h��������(�������(�������h��������(������������������������������� � (������ � (�B�������������� 2026-09-19T04:01:09Z