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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-04 21:32:30 UTC
NP-MRD IDNP0000539
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Methylhistidine
Description1-Methylhistidine, also known as 1-MHis or 1MH, belongs to the class of organic compounds known as histidine and derivatives. 1MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as pi-methylhistidine) or 3-methylhistidine (3MH; tau-methylhistidine), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine and other histidine-containing peptides such as anserine. In particular, older literature (mostly prior to the year 2000) designated anserine (Npi methylated) as beta-alanyl-N1-methyl-histidine, whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methyl-histidine. As a result, many papers published prior to the year 2000 incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really were referring to 3MH (PMID: 24137022 ). Recent discoveries have shown that 1MH is produced in essentially all mammals (and other vertebrates) via the enzyme known as METTL9 (PMID: 33563959 ). METTL9 is a broad-specificity methyltransferase that mediates the formation of the majority of 1MH present in mammalian proteomes. METTL9-catalyzed methylation requires a His-x-His (HxH) motif, where "x" is a small amino acid. This HxH motif is found in a number of abundant mammalian proteins such as ARMC6, S100A9, and NDUFB3 (PMID: 33563959 ). Because of its abundance in many muscle-related proteins, 1MH has been found to be a good biomarker for the consumption of meat (PMID: 21527577 ). Dietary studies have shown that poultry consumption (p-trend = 0.0006) And chicken consumption (p-trend = 0.0003) Are associated with increased levels of 1MH in human plasma (PMID: 30018457 ). The consumption of fish, especially salmon and cod, has also been shown to increase the levels of 1MH in serum and urine (PMID: 31401679 ). As a general rule, urinary 1MH is associated with white meat intake (p< 0.001), Whereas urinary 3MH is associated with red meat intake (p< 0.001) (PMID: 34091671 ).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acidChEBI
Pi-methylhistidineChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoateGenerator
1 MethylhistidineHMDB
1-Methyl histidineHMDB
1-Methyl-histidineHMDB
1-Methyl-L-histidineHMDB
1-MHisHMDB
1-N-Methyl-L-histidineHMDB
L-1-MethylhistidineHMDB
N1-Methyl-L-histidineHMDB
1-Methylhistidine dihydrochlorideHMDB
1-MethylhistidineChEBI
Chemical FormulaC7H11N3O2
Average Mass169.1811 Da
Monoisotopic Mass169.08513 Da
IUPAC Name(2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
Traditional Name1 methylhistidine
CAS Registry Number332-80-9
SMILES
CN1C=NC(C[C@H](N)C(O)=O)=C1
InChI Identifier
InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
InChI KeyBRMWTNUJHUMWMS-LURJTMIESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-08View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-01-08View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Prunus domesticaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point249http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.93 g/LALOGPS
logP-3ALOGPS
logP-3.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.39 m³·mol⁻¹ChemAxon
Polarizability17.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000001
DrugBank IDDB04151
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093588
KNApSAcK IDC00052105
Chemspider ID83153
KEGG Compound IDC01152
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylhistidine
METLIN ID3741
PubChem Compound92105
PDB IDNot Available
ChEBI ID50599
Good Scents IDNot Available
References
General References
  1. Colombani PC, Kovacs E, Frey-Rindova P, Frey W, Langhans W, Arnold M, Wenk C: Metabolic effects of a protein-supplemented carbohydrate drink in marathon runners. Int J Sport Nutr. 1999 Jun;9(2):181-201. [PubMed:10362454 ]
  2. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
  3. Myint T, Fraser GE, Lindsted KD, Knutsen SF, Hubbard RW, Bennett HW: Urinary 1-methylhistidine is a marker of meat consumption in Black and in White California Seventh-day Adventists. Am J Epidemiol. 2000 Oct 15;152(8):752-5. [PubMed:11052553 ]
  4. Giesecke K, Magnusson I, Ahlberg M, Hagenfeldt L, Wahren J: Protein and amino acid metabolism during early starvation as reflected by excretion of urea and methylhistidines. Metabolism. 1989 Dec;38(12):1196-200. [PubMed:2593832 ]
  5. Vranic L, Granic P, Rajic Z: Basic amino acid in the pathogenesis of caries. Acta Stomatol Croat. 1991;25(2):71-6. [PubMed:1819935 ]
  6. Sjolin J, Stjernstrom H, Henneberg S, Hambraeus L, Friman G: Evaluation of urinary 3-methylhistidine excretion in infection by measurements of 1-methylhistidine and the creatinine ratios. Am J Clin Nutr. 1989 Jan;49(1):62-70. [PubMed:2912013 ]
  7. COCKS DH, DENNIS PO, NELSON TH: ISOLATION OF 3-METHYL HISTIDINE FROM WHALEMEAT EXTRACT AND THE PREPARATION OF SOME DERIVATIVES. Nature. 1964 Apr 11;202:184-5. [PubMed:14156296 ]
  8. Dohm GL, Williams RT, Kasperek GJ, van Rij AM: Increased excretion of urea and N tau -methylhistidine by rats and humans after a bout of exercise. J Appl Physiol Respir Environ Exerc Physiol. 1982 Jan;52(1):27-33. [PubMed:7061274 ]
  9. Garlick PJ, McNurlan MA, Bark T, Lang CH, Gelato MC: Hormonal regulation of protein metabolism in relation to nutrition and disease. J Nutr. 1998 Feb;128(2 Suppl):356S-359S. [PubMed:9478024 ]
  10. Tuma P, Samcova E, Balinova P: Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jul 5;821(1):53-9. [PubMed:15899597 ]
  11. Dunnett M, Harris RC: High-performance liquid chromatographic determination of imidazole dipeptides, histidine, 1-methylhistidine and 3-methylhistidine in equine and camel muscle and individual muscle fibres. J Chromatogr B Biomed Sci Appl. 1997 Jan 10;688(1):47-55. [PubMed:9029312 ]
  12. Betto P, Ricciarello G, Pichini S, Dello Strologo L, Rizzoni G: High-performance liquid chromatography-electrochemical detection of 3-methylhistidine in human urine. J Chromatogr. 1992 Dec 23;584(2):256-60. [PubMed:1484110 ]
  13. Boldyrev AA, Aldini G, Derave W: Physiology and pathophysiology of carnosine. Physiol Rev. 2013 Oct;93(4):1803-45. doi: 10.1152/physrev.00039.2012. [PubMed:24137022 ]
  14. Davydova E, Shimazu T, Schuhmacher MK, Jakobsson ME, Willemen HLDM, Liu T, Moen A, Ho AYY, Malecki J, Schroer L, Pinto R, Suzuki T, Gronsberg IA, Sohtome Y, Akakabe M, Weirich S, Kikuchi M, Olsen JV, Dohmae N, Umehara T, Sodeoka M, Siino V, McDonough MA, Eijkelkamp N, Schofield CJ, Jeltsch A, Shinkai Y, Falnes PO: The methyltransferase METTL9 mediates pervasive 1-methylhistidine modification in mammalian proteomes. Nat Commun. 2021 Feb 9;12(1):891. doi: 10.1038/s41467-020-20670-7. [PubMed:33563959 ]
  15. Cross AJ, Major JM, Sinha R: Urinary biomarkers of meat consumption. Cancer Epidemiol Biomarkers Prev. 2011 Jun;20(6):1107-11. doi: 10.1158/1055-9965.EPI-11-0048. Epub 2011 Apr 28. [PubMed:21527577 ]
  16. Mitry P, Wawro N, Rohrmann S, Giesbertz P, Daniel H, Linseisen J: Plasma concentrations of anserine, carnosine and pi-methylhistidine as biomarkers of habitual meat consumption. Eur J Clin Nutr. 2019 May;73(5):692-702. doi: 10.1038/s41430-018-0248-1. Epub 2018 Jul 17. [PubMed:30018457 ]
  17. Hagen IV, Helland A, Bratlie M, Midttun O, McCann A, Sveier H, Rosenlund G, Mellgren G, Ueland PM, Gudbrandsen OA: TMAO, creatine and 1-methylhistidine in serum and urine are potential biomarkers of cod and salmon intake: a randomised clinical trial in adults with overweight or obesity. Eur J Nutr. 2020 Aug;59(5):2249-2259. doi: 10.1007/s00394-019-02076-4. Epub 2019 Aug 10. [PubMed:31401679 ]
  18. Said MY, Rodriguez-Nino A, Post A, Schutten JC, Kieneker LM, Gomes-Neto AW, van Londen M, Oste MC, Borgonjen-van den Berg KJ, Nolte IM, van den Berg E, de Blaauw P, van der Krogt J, Heiner-Fokkema MR, Navis G, Yard BA, Bakker SJ: Meat intake and risk of mortality and graft failure in kidney transplant recipients. Am J Clin Nutr. 2021 Jun 5. pii: 6294068. doi: 10.1093/ajcn/nqab185. [PubMed:34091671 ]