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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-04 16:09:46 UTC
Update Date2022-03-07 03:18:15 UTC
HMDB IDHMDB0240347
Secondary Accession NumbersNone
Metabolite Identification
Common NameN6-Carboxymethyllysine
DescriptionN6-Carboxymethyllysine (CML), also known as epsilon-(carboxymethyl)lysine, belongs to the class of organic compounds known as L-alpha-amino acids. These are alpha-amino acids which have the L-configuration of the alpha-carbon atom. CML is a Maillard reaction product, or dietary advanced glycation end-products (d-AGE), formed as a result of the thermal treatment of foods. Due to its chemical stability and its ubiquity in foods and in vivo, CML is used as a biomarker for the ingestion of thermally treated foods. CML is metabolized by intestinal bacteria under anaerobic conditions (PMID: 31091091 ).
Structure
Data?1573757150
Synonyms
ValueSource
N(6)-CarboxymethyllysineChEBI
N(epsilon)-(Carboxymethyl)lysineChEBI
NECMLChEBI
N(epsilon)-Carboxymethyl-L-lysineChEBI
N(epsilon)-CarboxymethyllysineHMDB
CarboxymethyllysineHMDB
Carboxymethyl-lysineHMDB
(2S)-2-Amino-6-(carboxymethylamino)hexanoic acidHMDB
N6-(Carboxymethyl)-L-lysineHMDB
N6-(Carboxymethyl)lysineHMDB
Nepsilon-(carboxymethyl)lysineHMDB
Nε-(carboxymethyl)lysineHMDB
epsilon-(Carboxymethyl)lysineHMDB
Ε-(carboxymethyl)lysineHMDB
CMLHMDB
N-epsilon-CarboxymethyllysineHMDB
N-Ε-carboxymethyllysineHMDB
N6-CarboxymethyllysineHMDB
Chemical FormulaC8H16N2O4
Average Molecular Weight204.226
Monoisotopic Molecular Weight204.111007003
IUPAC Name(2S)-2-amino-6-[(carboxymethyl)amino]hexanoic acid
Traditional NameN(6)-carboxymethyllysine
CAS Registry Number5746-04-3
SMILES
N[C@@H](CCCCNCC(O)=O)C(O)=O
InChI Identifier
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 KeyNUXSIDPKKIEIMI-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-3ALOGPS
logP-5.5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.61ChemAxon
pKa (Strongest Basic)10.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area112.65 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity48.67 m³·mol⁻¹ChemAxon
Polarizability21.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+144.15330932474
DeepCCS[M-H]-140.32630932474
DeepCCS[M-2H]-178.03630932474
DeepCCS[M+Na]+153.57930932474
AllCCS[M+H]+144.132859911
AllCCS[M+H-H2O]+140.532859911
AllCCS[M+NH4]+147.432859911
AllCCS[M+Na]+148.332859911
AllCCS[M-H]-144.632859911
AllCCS[M+Na-2H]-145.632859911
AllCCS[M+HCOO]-146.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N6-CarboxymethyllysineN[C@@H](CCCCNCC(O)=O)C(O)=O2714.4Standard polar33892256
N6-CarboxymethyllysineN[C@@H](CCCCNCC(O)=O)C(O)=O1827.4Standard non polar33892256
N6-CarboxymethyllysineN[C@@H](CCCCNCC(O)=O)C(O)=O2021.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N6-Carboxymethyllysine,1TMS,isomer #1C[Si](C)(C)OC(=O)CNCCCC[C@H](N)C(=O)O1981.9Semi standard non polar33892256
N6-Carboxymethyllysine,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CCCCNCC(=O)O1941.5Semi standard non polar33892256
N6-Carboxymethyllysine,1TMS,isomer #3C[Si](C)(C)N[C@@H](CCCCNCC(=O)O)C(=O)O2042.1Semi standard non polar33892256
N6-Carboxymethyllysine,1TMS,isomer #4C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)CC(=O)O2070.9Semi standard non polar33892256
N6-Carboxymethyllysine,2TMS,isomer #1C[Si](C)(C)OC(=O)CNCCCC[C@H](N)C(=O)O[Si](C)(C)C1960.6Semi standard non polar33892256
N6-Carboxymethyllysine,2TMS,isomer #2C[Si](C)(C)N[C@@H](CCCCNCC(=O)O[Si](C)(C)C)C(=O)O2069.4Semi standard non polar33892256
N6-Carboxymethyllysine,2TMS,isomer #3C[Si](C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O)[Si](C)(C)C2083.3Semi standard non polar33892256
N6-Carboxymethyllysine,2TMS,isomer #4C[Si](C)(C)N[C@@H](CCCCNCC(=O)O)C(=O)O[Si](C)(C)C2015.7Semi standard non polar33892256
N6-Carboxymethyllysine,2TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(CC(=O)O)[Si](C)(C)C2031.6Semi standard non polar33892256
N6-Carboxymethyllysine,2TMS,isomer #6C[Si](C)(C)N([C@@H](CCCCNCC(=O)O)C(=O)O)[Si](C)(C)C2180.7Semi standard non polar33892256
N6-Carboxymethyllysine,2TMS,isomer #7C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O)[Si](C)(C)C)C(=O)O2126.8Semi standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2057.7Semi standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2123.7Standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2387.5Standard polar33892256
N6-Carboxymethyllysine,3TMS,isomer #2C[Si](C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C2041.9Semi standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #2C[Si](C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C2100.7Standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #2C[Si](C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C2904.2Standard polar33892256
N6-Carboxymethyllysine,3TMS,isomer #3C[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2195.9Semi standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #3C[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2158.6Standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #3C[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2549.2Standard polar33892256
N6-Carboxymethyllysine,3TMS,isomer #4C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O2150.6Semi standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #4C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O2120.7Standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #4C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O2632.5Standard polar33892256
N6-Carboxymethyllysine,3TMS,isomer #5C[Si](C)(C)OC(=O)[C@H](CCCCNCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C2188.1Semi standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #5C[Si](C)(C)OC(=O)[C@H](CCCCNCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C2099.4Standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #5C[Si](C)(C)OC(=O)[C@H](CCCCNCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C2554.8Standard polar33892256
N6-Carboxymethyllysine,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O)[Si](C)(C)C)C(=O)O[Si](C)(C)C2096.3Semi standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O)[Si](C)(C)C)C(=O)O[Si](C)(C)C2126.6Standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O)[Si](C)(C)C)C(=O)O[Si](C)(C)C2526.5Standard polar33892256
N6-Carboxymethyllysine,3TMS,isomer #7C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CC(=O)O2242.3Semi standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #7C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CC(=O)O2172.6Standard non polar33892256
N6-Carboxymethyllysine,3TMS,isomer #7C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CC(=O)O2675.1Standard polar33892256
N6-Carboxymethyllysine,4TMS,isomer #1C[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2198.9Semi standard non polar33892256
N6-Carboxymethyllysine,4TMS,isomer #1C[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2201.4Standard non polar33892256
N6-Carboxymethyllysine,4TMS,isomer #1C[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2240.1Standard polar33892256
N6-Carboxymethyllysine,4TMS,isomer #2C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2108.7Semi standard non polar33892256
N6-Carboxymethyllysine,4TMS,isomer #2C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2157.8Standard non polar33892256
N6-Carboxymethyllysine,4TMS,isomer #2C[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2279.9Standard polar33892256
N6-Carboxymethyllysine,4TMS,isomer #3C[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2275.0Semi standard non polar33892256
N6-Carboxymethyllysine,4TMS,isomer #3C[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2234.4Standard non polar33892256
N6-Carboxymethyllysine,4TMS,isomer #3C[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2442.5Standard polar33892256
N6-Carboxymethyllysine,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCCN(CC(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2267.8Semi standard non polar33892256
N6-Carboxymethyllysine,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCCN(CC(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2216.9Standard non polar33892256
N6-Carboxymethyllysine,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCCN(CC(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2398.5Standard polar33892256
N6-Carboxymethyllysine,5TMS,isomer #1C[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2333.5Semi standard non polar33892256
N6-Carboxymethyllysine,5TMS,isomer #1C[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2255.7Standard non polar33892256
N6-Carboxymethyllysine,5TMS,isomer #1C[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2208.1Standard polar33892256
N6-Carboxymethyllysine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNCCCC[C@H](N)C(=O)O2253.8Semi standard non polar33892256
N6-Carboxymethyllysine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCNCC(=O)O2199.3Semi standard non polar33892256
N6-Carboxymethyllysine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCCNCC(=O)O)C(=O)O2292.5Semi standard non polar33892256
N6-Carboxymethyllysine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)CC(=O)O2324.8Semi standard non polar33892256
N6-Carboxymethyllysine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2445.6Semi standard non polar33892256
N6-Carboxymethyllysine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCCNCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2570.2Semi standard non polar33892256
N6-Carboxymethyllysine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2556.9Semi standard non polar33892256
N6-Carboxymethyllysine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CCCCNCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2493.8Semi standard non polar33892256
N6-Carboxymethyllysine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(CC(=O)O)[Si](C)(C)C(C)(C)C2502.1Semi standard non polar33892256
N6-Carboxymethyllysine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N([C@@H](CCCCNCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C2635.2Semi standard non polar33892256
N6-Carboxymethyllysine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O2600.6Semi standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2744.3Semi standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2672.6Standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2664.6Standard polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2735.5Semi standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2673.7Standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2991.6Standard polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2885.2Semi standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2709.8Standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2740.3Standard polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2854.6Semi standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2663.1Standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2831.3Standard polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2861.9Semi standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2659.8Standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2747.6Standard polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2784.1Semi standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2657.4Standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2770.6Standard polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC(=O)O2911.9Semi standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC(=O)O2703.7Standard non polar33892256
N6-Carboxymethyllysine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC(=O)O2848.0Standard polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3107.4Semi standard non polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2908.6Standard non polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2651.5Standard polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3014.2Semi standard non polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2856.0Standard non polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2721.4Standard polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3144.7Semi standard non polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2914.7Standard non polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2772.6Standard polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(CC(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3132.8Semi standard non polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(CC(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2895.0Standard non polar33892256
N6-Carboxymethyllysine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(CC(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2750.4Standard polar33892256
N6-Carboxymethyllysine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3419.5Semi standard non polar33892256
N6-Carboxymethyllysine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3069.3Standard non polar33892256
N6-Carboxymethyllysine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2728.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N6-Carboxymethyllysine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N6-Carboxymethyllysine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Carboxymethyllysine 10V, Positive-QTOFsplash10-0a5i-2960000000-c1f9dc0a5b88f61b10a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Carboxymethyllysine 20V, Positive-QTOFsplash10-001i-9400000000-20449fa8c1f46d91fd422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Carboxymethyllysine 40V, Positive-QTOFsplash10-0ac0-9000000000-69659eefcdd0c58f02c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Carboxymethyllysine 10V, Negative-QTOFsplash10-0udi-0090000000-2cc3f54c600fdcda0c9d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Carboxymethyllysine 20V, Negative-QTOFsplash10-0udi-0970000000-beb54ba3fb5157275eb82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Carboxymethyllysine 40V, Negative-QTOFsplash10-060c-9000000000-b14887973901def789e62021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID110350
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound123800
PDB IDNot Available
ChEBI ID53014
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bui TPN, Troise AD, Fogliano V, de Vos WM: Anaerobic Degradation of N-epsilon-Carboxymethyllysine, a Major Glycation End-Product, by Human Intestinal Bacteria. J Agric Food Chem. 2019 Jun 12;67(23):6594-6602. doi: 10.1021/acs.jafc.9b02208. Epub 2019 May 28. [PubMed:31091091 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]