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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-06-11 23:17:42 UTC
HMDB IDHMDB00001
Secondary Accession Numbers
  • HMDB04935
  • HMDB06703
  • HMDB06704
Metabolite Identification
Common Name1-Methylhistidine
DescriptionOne-methylhistidine (1-MHis) is derived mainly from the anserine of dietary flesh sources, especially poultry. The enzyme, carnosinase, splits anserine into b-alanine and 1-MHis. High levels of 1-MHis tend to inhibit the enzyme carnosinase and increase anserine levels. Conversely, genetic variants with deficient carnosinase activity in plasma show increased 1-MHis excretions when they consume a high meat diet. Reduced serum carnosinase activity is also found in patients with Parkinson's disease and multiple sclerosis and patients following a cerebrovascular accident. Vitamin E deficiency can lead to 1-methylhistidinuria from increased oxidative effects in skeletal muscle.
Structure
Thumb
Synonyms
  1. 1 Methylhistidine
  2. 1-Methyl histidine
  3. 1-Methyl-Histidine
  4. 1-Methyl-L-histidine
  5. 1-MHis
  6. 1-N-Methyl-L-histidine
  7. L-1-Methylhistidine
  8. N1-Methyl-L-histidine
  9. Pi-methylhistidine
Chemical FormulaC7H11N3O2
Average Molecular Weight169.1811
Monoisotopic Molecular Weight169.085126611
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
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
Substituents
  • Aminoimidazole
  • Carboxylic Acid
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility6.93ALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.39 m3·mol-1ChemAxon
Polarizability16.95 Å3ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
Histidine MetabolismSMP00044map00340
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.7 +/- 1.9 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified14.4 +/- 2.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified19.6 +/- 2.6 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified12.7 +/- 2.9 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified20.2 +/- 4.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified9.1 +/- 7.2 uMChildren (1-13 years old)Not SpecifiedNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified4.0 +/- 8.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified4.0 +/- 1.74 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified26.34 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableNot AvailableMaleNormal details
UrineDetected and Quantified17.74-153.77 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified8.3 (2.4-28.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified15.9 +/- 19.5 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified30.0 +/- 43.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.6 +/- 2.7 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified2.3 +/- 5.1 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified46.1 +/- 53.5 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified15.9 +/- 19.5 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified28.1 +/- 31.8 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified1.3 +/- 2.76 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified45.5 +/- 41.6 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified33.6 +/- 36.4 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified28.8 +/- 18.2 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified83.1 +/- 21.7 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified10.66 +/- 2.68 uMElderly (>65 years old)Both
Alzheimer's disease
details
Cerebrospinal Fluid (CSF)Detected and Quantified2.6 +/- 1.13 uMAdult (>18 years old)BothAlzheimer's disease details
UrineDetected and Quantified10.9 +/- 10.1 umol/mmol creatinineAdult (>18 years old)BothObesity details
UrineDetected and Quantified17.5 +/- 25.7 umol/mmol creatinineAdult (>18 years old)BothDiabetes details
UrineDetected and Quantified15.7 +/- 4.04 umol/mmol creatinineAdult (>18 years old)Both
Alzheimer's disease
details
UrineDetected and Quantified40 +/- 2.6 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia details
UrineDetected and Quantified31 +/- 11 umol/mmol creatinineAdult (>18 years old)BothMaple syrup urine disease details
UrineDetected and Quantified50.3 +/- 9.9 umol/mmol creatinineAdult (>18 years old)BothAminoaciduria details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479
Diabetes mellitus type 2
  1. 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
Kidney disease
  1. Raj DS, Ouwendyk M, Francoeur R, Pierratos A: Plasma amino acid profile on nocturnal hemodialysis. Blood Purif. 2000;18(2):97-102. Pubmed: 10838467
Obesity
  1. 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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012119
KNApSAcK IDNot Available
Chemspider ID83153
KEGG Compound IDC01152
BioCyc IDCPD-1823
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00001
Metagene LinkHMDB00001
METLIN ID3741
PubChem Compound92105
PDB IDHIC
ChEBI ID50599
References
Synthesis ReferenceJain, Rahul; Cohen, Louis A. Regiospecific alkylation of histidine and histamine at N-1 (t).Tetrahedron (1996), 52(15), 5363-70.
Material Safety Data Sheet (MSDS)Download (PDF)
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. 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

Enzymes

General function:
Involved in metallopeptidase activity
Specific function:
Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
Gene Name:
CNDP1
Uniprot ID:
Q96KN2
Molecular weight:
56691.6
References
  1. Fleisher LD, Rassin DK, Wisniewski K, Salwen HR: Carnosinase deficiency: a new variant with high residual activity. Pediatr Res. 1980 Apr;14(4 Pt 1):269-71. Pubmed: 7375183
General function:
Involved in protein methyltransferase activity
Specific function:
Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:
PRMT3
Uniprot ID:
O60678
Molecular weight:
59902.7
References
  1. Raghavan M, Lindberg U, Schutt C: The use of alternative substrates in the characterization of actin-methylating and carnosine-methylating enzymes. Eur J Biochem. 1992 Nov 15;210(1):311-8. Pubmed: 1446680