Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:47:30 UTC
Update Date2023-05-30 20:56:03 UTC
HMDB IDHMDB0032055
Secondary Accession Numbers
  • HMDB32055
Metabolite Identification
Common NameN-Acetylhistidine
DescriptionN-Acetyl-L-histidine or N-Acetylhistidine, 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 its terminal nitrogen atom. N-Acetylhistidine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylhistidine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-histidine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylhistidine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free histidine can also occur. In particular, N-Acetylhistidine can be biosynthesized from L-histidine and acetyl-CoA by the enzyme histidine N-acetyltransferase (EC 2.3.1.33). 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?1677000094
Synonyms
ValueSource
N-Acetyl histidineChEBI
N-alpha-L-HistidineChEBI
N-Hydroxy-aabpChEBI
N-a-L-HistidineGenerator
N-Α-L-histidineGenerator
N-Acetylhistidine, (DL)-isomerHMDB
N-Acetylhistidine monohydrateHMDB
(2S)-2-Acetamido-3-(1H-imidazol-5-yl)propanoic acidHMDB
(2S)-2-Acetamido-3-(1H-imidazol-5-yl)propionic acidHMDB
(S)-2-Acetamido-3-(1H-imidazol-4-yl)propanoicacidHMDB
N-Acetyl-L-histidineHMDB
N-alpha-Acetyl-L-histidineHMDB
N-Α-acetyl-L-histidineHMDB
N2-AcetylhistidineHMDB
Nalpha-acetyl-L-histidineHMDB
Nalpha-acetylhistidineHMDB
Nα-acetyl-L-histidineHMDB
Nα-acetylhistidineHMDB
alpha-N-Acetyl-L-histidineHMDB
Α-N-acetyl-L-histidineHMDB
N-AcetylhistidineChEBI
Chemical FormulaC8H11N3O3
Average Molecular Weight197.194
Monoisotopic Molecular Weight197.080041226
IUPAC Name(2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid
Traditional Name(2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid
CAS Registry Number2497-02-1
SMILES
CC(=O)N[C@@H](CC1=CNC=N1)C(O)=O
InChI Identifier
InChI=1S/C8H11N3O3/c1-5(12)11-7(8(13)14)2-6-3-9-4-10-6/h3-4,7H,2H2,1H3,(H,9,10)(H,11,12)(H,13,14)/t7-/m0/s1
InChI KeyKBOJOGQFRVVWBH-ZETCQYMHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point187 °CNot Available
Boiling Point620.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility11360 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-1.600 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.09 g/LALOGPS
logP-0.34ALOGPS
logP-2.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)6.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.08 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity46.94 m³·mol⁻¹ChemAxon
Polarizability18.82 ųChemAxon
Number of Rings1ChemAxon
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]+137.13730932474
DeepCCS[M-H]-134.74230932474
DeepCCS[M-2H]-169.7630932474
DeepCCS[M+Na]+144.6730932474
AllCCS[M+H]+143.432859911
AllCCS[M+H-H2O]+139.532859911
AllCCS[M+NH4]+147.132859911
AllCCS[M+Na]+148.232859911
AllCCS[M-H]-141.032859911
AllCCS[M+Na-2H]-141.732859911
AllCCS[M+HCOO]-142.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-AcetylhistidineCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O3051.0Standard polar33892256
N-AcetylhistidineCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O1875.1Standard non polar33892256
N-AcetylhistidineCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O2083.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylhistidine,1TMS,isomer #1CC(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C1953.8Semi standard non polar33892256
N-Acetylhistidine,1TMS,isomer #2CC(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C1946.6Semi standard non polar33892256
N-Acetylhistidine,1TMS,isomer #3CC(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O2077.9Semi standard non polar33892256
N-Acetylhistidine,2TMS,isomer #1CC(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C1938.8Semi standard non polar33892256
N-Acetylhistidine,2TMS,isomer #1CC(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2014.9Standard non polar33892256
N-Acetylhistidine,2TMS,isomer #2CC(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C2113.2Semi standard non polar33892256
N-Acetylhistidine,2TMS,isomer #2CC(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C1951.4Standard non polar33892256
N-Acetylhistidine,2TMS,isomer #3CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C2077.8Semi standard non polar33892256
N-Acetylhistidine,2TMS,isomer #3CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C2042.3Standard non polar33892256
N-Acetylhistidine,3TMS,isomer #1CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2093.1Semi standard non polar33892256
N-Acetylhistidine,3TMS,isomer #1CC(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2047.1Standard non polar33892256
N-Acetylhistidine,1TBDMS,isomer #1CC(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C2187.3Semi standard non polar33892256
N-Acetylhistidine,1TBDMS,isomer #2CC(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2173.3Semi standard non polar33892256
N-Acetylhistidine,1TBDMS,isomer #3CC(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O2343.2Semi standard non polar33892256
N-Acetylhistidine,2TBDMS,isomer #1CC(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2398.1Semi standard non polar33892256
N-Acetylhistidine,2TBDMS,isomer #1CC(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2464.8Standard non polar33892256
N-Acetylhistidine,2TBDMS,isomer #2CC(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C2586.8Semi standard non polar33892256
N-Acetylhistidine,2TBDMS,isomer #2CC(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C2362.3Standard non polar33892256
N-Acetylhistidine,2TBDMS,isomer #3CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2558.1Semi standard non polar33892256
N-Acetylhistidine,2TBDMS,isomer #3CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2436.2Standard non polar33892256
N-Acetylhistidine,3TBDMS,isomer #1CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2744.9Semi standard non polar33892256
N-Acetylhistidine,3TBDMS,isomer #1CC(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2653.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylhistidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylhistidine 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 - N-Acetylhistidine 20V, Negative-QTOFsplash10-03di-4900000000-7dfc9fc16ac2951b95022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylhistidine 10V, Negative-QTOFsplash10-03di-1900000000-f7a336a0bb3b9bbb97e62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylhistidine 35V, Positive-QTOFsplash10-03di-1900000000-b0d3eefbbb19800713842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylhistidine 35V, Negative-QTOFsplash10-03di-0900000000-fbdb976de813e485a0502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylhistidine 40V, Negative-QTOFsplash10-001l-9100000000-5a50d7a1e623f2b3ad432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylhistidine 30V, Negative-QTOFsplash10-03e9-9600000000-c0d983087d28441957482021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylhistidine 10V, Positive-QTOFsplash10-0k9t-0900000000-3f38d32bce161a4e5d4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylhistidine 20V, Positive-QTOFsplash10-03dr-0900000000-092c7fb7959085278f1c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylhistidine 40V, Positive-QTOFsplash10-01qc-9300000000-a303332b1163ebaf0e9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylhistidine 10V, Negative-QTOFsplash10-0udi-0900000000-38551fb9b9676dd589042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylhistidine 20V, Negative-QTOFsplash10-0a4i-9800000000-7438d910d167860d71592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylhistidine 40V, Negative-QTOFsplash10-052f-9100000000-ef73aa98a219c40481e82021-09-22Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
UrineDetected and Quantified8.13 (3.72-9.89) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008762
KNApSAcK IDNot Available
Chemspider ID68142
KEGG Compound IDC02997
BioCyc IDCPD-424
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75619
PDB IDNot Available
ChEBI ID16437
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1691611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
  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 ]
  3. 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 ]
  4. Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
  5. Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
  6. 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 ]
  7. 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 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .