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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-07-01 14:26:38 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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • Eubacteria
  • 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 ]