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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:27:44 UTC
HMDB IDHMDB0000206
Secondary Accession Numbers
  • HMDB00206
Metabolite Identification
Common NameN6-Acetyl-L-lysine
DescriptionN-epsilon-Acetyl-L-lysine also known as Nepsilon-Acetyllysine or N6-Acetyllysine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at one of its nitrogen atoms. N-epsilon-Acetyl-L-lysine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-epsilon-Acetyl-L-lysine is a biologically available sidechain, N-capped form of the proteinogenic alpha amino acid L-lysine. Unlike L-lysine, acetylated lysine derivatives such as N-epsilon-Acetyl-L-lysine are zwitterionic compounds. These are molecules that contains an equal number of positively- and negatively-charged functional groups. N-epsilon-Acetyl-L-lysine is found naturally in eukaryotes ranging from yeast to plants to humans. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins (often histones) by specific hydrolases. N-epsilon-Acetyl-L-lysine can be biosynthesized from L-lysine and acetyl-CoA via the enzyme known as Lysine N-acetyltransferase. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins – either N-terminal or N-alpha acetylation or N6 (sidechain) acetylation. Side-chain acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. By modifying chromatin proteins and transcription-related factors, these acetylases are believed to regulate the transcription of many genes. The best-characterized mechanism is acetylation, catalyzed by histone acetyltransferase (HAT) enzymes. HATs function enzymatically by transferring an acetyl group from acetyl-coenzyme A (acetyl-CoA) to the amino group of certain lysine side chains within a histone's basic N-terminal tail region. Within a histone octamer, these regions extend out from the associated globular domains, and in the context of a nucleosome, they are believed to bind the DNA through charge interactions (positively charged histone tails associated with negatively charged DNA) or mediate interactions between nucleosomes. Lysine acetylation, which neutralizes part of a tail region's positive charge, is postulated to weaken histone-DNA or nucleosome-nucleosome interactions and/or signal a conformational change, thereby destabilizing nucleosome structure or arrangement and giving other nuclear factors, such as the transcription complex, more access to a genetic locus. In agreement with this is the fact that acetylated chromatin has long been associated with states of transcriptional activation. Specific recognition of N6-acetyl-L-lysine is a conserved function of all bromodomains found in different proteins, recognized as an emerging intracellular signalling mechanism that plays critical roles in regulating gene transcription, cell-cycle progression, apoptosis, DNA repair, and cytoskeletal organization (PMID: 9169194 , 10827952 , 17340003 , 16247734 , 9478947 , 10839822 ). N-acetylated amino acids, such as N-epsilon-Acetyl-L-lysine can be released by an N-acylpeptide hydrolase from histones going through proteolytic degradation (PMID: 16465618 ). Many N-acetylamino acids are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).
Structure
Data?1582752116
Synonyms
ValueSource
(2S)-6-(Acetylamino)-2-aminohexanoic acidChEBI
N(6)-ACETYLLYSINEChEBI
N(zeta)-AcetyllysineChEBI
N-epsilon-Acetyl-L-lysineChEBI
N-Epsilon-AcetyllysineChEBI
N(epsilon)-Acetyl-L-lysineChEBI
N(zeta)-Acetyl-L-lysineChEBI
(2S)-6-(Acetylamino)-2-aminohexanoateGenerator
N(Z)-AcetyllysineGenerator
N(Ζ)-acetyllysineGenerator
N(Z)-Acetyl-L-lysineGenerator
N(Ζ)-acetyl-L-lysineGenerator
e-Acetyl-L-lysineHMDB
e-N-Acetyl-L-lysineHMDB
e-N-AcetyllysineHMDB
epsilon-Acetyl-L-lysineHMDB
epsilon-N-Acetyl-L-lysineHMDB
epsilon-N-AcetyllysineHMDB
L-e-N-AcetyllysineHMDB
L-epsilon-N-AcetyllysineHMDB
N-e-Acetyl-L-lysineHMDB
N-e-AcetyllysineHMDB
N6-AcetyllysineHMDB
Ne-acetyl-L-lysineHMDB
Ne-acetyllysineHMDB
Omega-N-acetyl-L-lysineHMDB
W-N-Acetyl-L-lysineHMDB
N(6)-AcetyllsineHMDB
Omega-acetyllsineHMDB
(2S)-6-Acetamido-2-aminohexanoic acidHMDB
6-Acetamido-2-aminohexanoic acidHMDB
L-Ε-N-acetyllysineHMDB
Nepsilon-acetyl-L-lysineHMDB
Nepsilon-acetyllysineHMDB
Nε-acetyl-L-lysineHMDB
Nε-acetyllysineHMDB
Ε-acetyl-L-lysineHMDB
Ε-N-acetyl-L-lysineHMDB
Ε-N-acetyllysineHMDB
Ω-N-acetyl-L-lysineHMDB
N6-Acetyl-L-lysineChEBI
Chemical FormulaC8H16N2O3
Average Molecular Weight188.2242
Monoisotopic Molecular Weight188.116092388
IUPAC Name(2S)-2-amino-6-acetamidohexanoic acid
Traditional NameN6-acetyllysine
CAS Registry Number692-04-6
SMILES
CC(=O)NCCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C8H16N2O3/c1-6(11)10-5-3-2-4-7(9)8(12)13/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1
InChI KeyDTERQYGMUDWYAZ-ZETCQYMHSA-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
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8346 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-MetCCS_train_neg139.7530932474
DeepCCS[M+H]+MetCCS_train_pos142.330932474
AllCCS[M-H]-Not Available139.75http://allccs.zhulab.cn/database/detail?ID=AllCCS00000010
AllCCS[M+H]+Not Available142.438http://allccs.zhulab.cn/database/detail?ID=AllCCS00000010
Predicted Molecular Properties
PropertyValueSource
Water Solubility17.5 g/LALOGPS
logP10(-2.6) g/LALOGPS
logP10(-3.2) g/LChemAxon
logS10(-1) g/LALOGPS
pKa (Strongest Acidic)2.43ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability20.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.38731661259
DarkChem[M-H]-139.74531661259
AllCCS[M+H]+143.04632859911
AllCCS[M-H]-142.03932859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N6-Acetyl-L-lysine,1TMS,#1CC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C1829.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TMS,#2CC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O1903.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TMS,#3CC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C1877.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TBDMS,#1CC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2103.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TBDMS,#2CC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2168.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
N6-Acetyl-L-lysine,1TBDMS,#3CC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2090.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (3 TMS)splash10-0002-9610000000-6e30cfdb2a70cc49f9832014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (Non-derivatized)splash10-0002-9610000000-6e30cfdb2a70cc49f9832017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N6-Acetyl-L-lysine GC-EI-TOF (Non-derivatized)splash10-004i-1900000000-e36d5532f4f0ed8ec34f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N6-Acetyl-L-lysine GC-EI-TOF (Non-derivatized)splash10-0002-9500000000-266c8b0fce84c71553b22017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9200000000-a186b34425c93ea31a662017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9110000000-255e47c2dfcdf6b614032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N6-Acetyl-L-lysine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004r-1900000000-4745f7cfa9eaaef208ad2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9000000000-635805826359aa05ec7c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-9000000000-8857489c6ac957c71a5d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-000i-0900000000-39f911570385230170462012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000j-0900000000-183e1f50c20603f14c032012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0002-1900000000-da02d0f8bd73b5b96b462012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0a4j-9400000000-8531cdbb4e8108dbec952012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0a4l-9000000000-94d72f2c644db8c0b5cd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-000i-0900000000-c6ff005564503774a8532012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-004i-3900000000-dffc604f608a010e711e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-001i-9000000000-d6bc330de42890c4c0912012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-001i-9000000000-8d68337bf7a8db380cd72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-001i-9000000000-1400569a447d5f66c3a82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-39f911570385230170462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOFsplash10-000j-0900000000-183e1f50c20603f14c032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOFsplash10-0002-1900000000-da02d0f8bd73b5b96b462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOFsplash10-0a4j-9400000000-8531cdbb4e8108dbec952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , negative-QTOFsplash10-0a4l-9000000000-94d72f2c644db8c0b5cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N6-Acetyl-L-lysine LC-ESI-QQ , positive-QTOFsplash10-000i-0900000000-c6ff005564503774a8532017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 10V, Positive-QTOFsplash10-0077-0900000000-e0d9659d3d504e9c8d812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 20V, Positive-QTOFsplash10-0ued-3900000000-ae84e0c568d22d7c62fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 40V, Positive-QTOFsplash10-001i-9100000000-848f804e26f5a4edfcfb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 10V, Negative-QTOFsplash10-000i-0900000000-545e3c760ee61913f3012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 20V, Negative-QTOFsplash10-05p2-3900000000-3a6e9f0c90d936bd6ae82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-Acetyl-L-lysine 40V, Negative-QTOFsplash10-052f-9000000000-33c2ede158e490bcc70f2017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.036-2.828 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified9.318 +/- 4.75 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque details
UrineDetected and Quantified10.141 +/- 3.949 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000476
KNApSAcK IDNot Available
Chemspider ID83801
KEGG Compound IDC02727
BioCyc IDCPD-567
BiGG IDNot Available
Wikipedia LinkAcetyllysine
METLIN ID5216
PubChem Compound92832
PDB IDNot Available
ChEBI ID17752
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1266461
References
Synthesis ReferenceBenoiton, Leo; Leclerc, Jean. An improved synthesis of e-N-acetyl-L-lysine and similar compounds. Canadian Journal of Chemistry (1965), 43(4), 991-3.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  2. Jacobson RH, Ladurner AG, King DS, Tjian R: Structure and function of a human TAFII250 double bromodomain module. Science. 2000 May 26;288(5470):1422-5. [PubMed:10827952 ]
  3. Armstrong MD, Robinow M: A case of hyperlysinemia: biochemical and clinical observations. Pediatrics. 1967 Apr;39(4):546-54. [PubMed:6022933 ]
  4. Crane-Robinson C, Hebbes TR, Clayton AL, Thorne AW: Chromosomal mapping of core histone acetylation by immunoselection. Methods. 1997 May;12(1):48-56. [PubMed:9169194 ]
  5. Jamonnak N, Fatkins DG, Wei L, Zheng W: N(epsilon)-methanesulfonyl-lysine as a non-hydrolyzable functional surrogate for N(epsilon)-acetyl-lysine. Org Biomol Chem. 2007 Mar 21;5(6):892-6. Epub 2007 Feb 5. [PubMed:17340003 ]
  6. Iwabata H, Yoshida M, Komatsu Y: Proteomic analysis of organ-specific post-translational lysine-acetylation and -methylation in mice by use of anti-acetyllysine and -methyllysine mouse monoclonal antibodies. Proteomics. 2005 Dec;5(18):4653-64. [PubMed:16247734 ]
  7. Hazen SL, d'Avignon A, Anderson MM, Hsu FF, Heinecke JW: Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to oxidize alpha-amino acids to a family of reactive aldehydes. Mechanistic studies identifying labile intermediates along the reaction pathway. J Biol Chem. 1998 Feb 27;273(9):4997-5005. [PubMed:9478947 ]
  8. Sterner DE, Berger SL: Acetylation of histones and transcription-related factors. Microbiol Mol Biol Rev. 2000 Jun;64(2):435-59. [PubMed:10839822 ]
  9. 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 ]
  10. Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
  11. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
  12. Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]