Nepsilon-(Carboxymethyl)lysine

Details

• Internal ID: 79fe6a5b-d05f-4500-baa7-5e51aa63b3b2
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids > L-alpha-amino acids
• IUPAC Name: (2S)-2-amino-6-(carboxymethylamino)hexanoic acid
• InChI: 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)/t6-/m0/s1
• InChI Key: NUXSIDPKKIEIMI-LURJTMIESA-N
• Popularity: 1,080 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₆N₂O₄
• Molecular Weight: 204.22 g/mol
• Exact Mass: 204.11100700 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: -5.20
• Atomic LogP (AlogP): -0.76
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• N(6)-carboxymethyllysine
• NECML
• Nepsilon-(carboxymethyl)lysine
• L-Lysine, N6-(carboxymethyl)-
• N(epsilon)-(Carboxymethyl)lysine
• (2S)-2-amino-6-(carboxymethylamino)hexanoic acid
• 70YDX3Z2O7
• CHEBI:53014
• N(epsilon)-carboxymethyl-L-lysine
• DTXSID80904133
• carboxymethyl-lysine
• RefChem:160764
• n(epsilon)-carboxymethyllysine
• DTXCID901332017
• 2-amino-6-((carboxymethyl)amino)hexanoic acid
• (2S)-2-azaniumyl-6-(carboxylatomethylazaniumyl)hexanoate
• Ne-Carboxymethyl-L-lysine
• N6-(Carboxymethyl)lysine
• N6-(carboxymethyl)-L-lysine
• N(6)-carboxymethyl-L-lysine
• N|A-(Carboxymethyl)-L-lysine
• (2S)-2-amino-6-[(carboxymethyl)amino]hexanoic acid
• N(6)-(carboxymethyl)-L-lysine
• N?-(1-Carboxymethyl)-L-lysine
• MFCD04114278
• (S)-2-Amino-6-((carboxymethyl)amino)hexanoic acid
• nepsilon-carboxymethyl-l-lysine
• NEpsilon-(1-Carboxymethyl)-L-lysine
• CML
• N6-Carboxymethyllysine
• n'-(carboxymethyl)lysine
• N|A-(Carboxymethyl)lysine
• Epitope ID:150904
• CML - carboxymethyl lysine
• UNII-70YDX3Z2O7
• SCHEMBL43621
• orb2283784
• N~6~-(Carboxymethyl)-L-lysine
• NUXSIDPKKIEIMI-LURJTMIESA-N
• N?-?(1-Carboxymethyl)-L-?lysine
• NSC824653
• AKOS015969256
• CML, N-epsilon-Carboxymethyl-L-lysine
• HY-W286743
• NSC-824653
• N epsilon -(1-Carboxymethyl)-L-lysine
• N.EPSILON.-(CARBOXYMETHYL)LYSINE
• DB-255698
• CS-0331741
• G84805
• T84435
• (S)-2-Amino-6-((carboxymethyl)amino)hexanoicacid
• F402228
• (2~{S})-2-azanyl-6-(2-hydroxy-2-oxoethylamino)hexanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6290	62.90%
Caco-2	-	0.9170	91.70%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5648	56.48%
OATP2B1 inhibitior	-	0.8483	84.83%
OATP1B1 inhibitior	+	0.9555	95.55%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9613	96.13%
P-glycoprotein inhibitior	-	0.9807	98.07%
P-glycoprotein substrate	-	0.8427	84.27%
CYP3A4 substrate	-	0.6549	65.49%
CYP2C9 substrate	-	0.5957	59.57%
CYP2D6 substrate	-	0.7409	74.09%
CYP3A4 inhibition	-	0.9376	93.76%
CYP2C9 inhibition	-	0.9595	95.95%
CYP2C19 inhibition	-	0.9518	95.18%
CYP2D6 inhibition	-	0.9655	96.55%
CYP1A2 inhibition	-	0.7766	77.66%
CYP2C8 inhibition	-	0.9824	98.24%
CYP inhibitory promiscuity	-	1.0000	100.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6813	68.13%
Eye corrosion	-	0.9259	92.59%
Eye irritation	-	0.8797	87.97%
Skin irritation	-	0.7828	78.28%
Skin corrosion	-	0.8814	88.14%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7710	77.10%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9237	92.37%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	-	0.7516	75.16%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8834	88.34%
Acute Oral Toxicity (c)	III	0.5697	56.97%
Estrogen receptor binding	-	0.8263	82.63%
Androgen receptor binding	-	0.8314	83.14%
Thyroid receptor binding	-	0.7857	78.57%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.8332	83.32%
PPAR gamma	-	0.6232	62.32%
Honey bee toxicity	-	0.9874	98.74%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.8739	87.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.45%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.33%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	94.22%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	92.81%	90.17%
CHEMBL2581	P07339	Cathepsin D	89.31%	98.95%
CHEMBL236	P41143	Delta opioid receptor	87.83%	99.35%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.81%	100.00%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	85.48%	94.01%
CHEMBL2514	O95665	Neurotensin receptor 2	85.28%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	85.20%	90.20%
CHEMBL4070	P19784	Casein kinase II alpha (prime)	84.02%	91.67%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.95%	97.21%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	83.15%	97.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.08%	91.11%
CHEMBL1938211	O15054	Lysine-specific demethylase 6B	83.07%	83.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.34%	94.45%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	82.29%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.68%	100.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	81.61%	92.29%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.08%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.81%	96.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.21%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.10%	91.19%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	80.00%	92.26%

Plants that contains it

• Sagittaria pygmaea

Cross-Links

• PubChem: 123800
• LOTUS: LTS0099397
• wikiData: Q76010404