Human Metabolome Database Version 3.5

Showing metabocard for 1-Methylhistidine (HMDB00001)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-07-24 11:48:59 -0600
HMDB ID HMDB00001
Secondary Accession Numbers
  • HMDB04935
  • HMDB06703
  • HMDB06704
Metabolite Identification
Common Name 1-Methylhistidine
Description One-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C7H11N3O2
Average Molecular Weight 169.1811
Monoisotopic Molecular Weight 169.085126611
IUPAC Name (2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
Traditional IUPAC Name 1 methylhistidine
CAS Registry Number 332-80-9
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 Key BRMWTNUJHUMWMS-LURJTMIESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
Substituents
  • Aminoimidazole
  • Carboxylic Acid
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 6.93 g/L ALOGPS
LogP -2.95 ALOGPS
LogP -3.1 ChemAxon
LogS -1.39 ALOGPS
pKa (strongest acidic) 1.96 ChemAxon
pKa (strongest basic) 9.25 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 81.14 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 42.39 ChemAxon
Polarizability 16.95 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
Pathways
Name SMPDB Link KEGG Link
Histidine Metabolism SMP00044 map00340 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
7.7 +/- 1.9 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
14.4 +/- 2.3 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
19.6 +/- 2.6 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
12.7 +/- 2.9 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
20.2 +/- 4.0 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
9.1 +/- 7.2 uM Children (1-13 year old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
4.0 +/- 8.0 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
4.0 +/- 1.74 uM Adult (>18 years old) Both Normal
Saliva Detected and Quantified
26.34 uM Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Not Available Male Normal
Urine Detected and Quantified
17.74-153.77 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
8.3 (2.4-28.4) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
15.9 +/- 19.5 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
30.0 +/- 43.0 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0019 - 0.0038 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
4.6 +/- 2.7 umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
2.3 +/- 5.1 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
46.1 +/- 53.5 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
15.9 +/- 19.5 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
28.1 +/- 31.8 umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
1.3 +/- 2.76 umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
45.5 +/- 41.6 umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
33.6 +/- 36.4 umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 28.8 +/- 18.2 uM Adult (>18 years old) Both Comment Kidney disease
Blood Detected and Quantified 83.1 +/- 21.7 uM Adult (>18 years old) Both Comment Kidney disease
Blood Detected and Quantified 10.66 +/- 2.68 uM Elderly (>65 years old) Both Comment Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 2.6 +/- 1.13 uM Adult (>18 years old) Both Alzheimer's disease
Urine Detected and Quantified 10.9 +/- 10.1 umol/mmol creatinine Adult (>18 years old) Both Obesity
Urine Detected and Quantified 17.5 +/- 25.7 umol/mmol creatinine Adult (>18 years old) Both Diabetes
Urine Detected and Quantified 0.0031 - 0.0042 umol/mmol creatinine Adult (>18 years old) Both ADPKD
Urine Detected and Quantified 15.7 +/- 4.04 umol/mmol creatinine Adult (>18 years old) Both Comment Alzheimer's disease
Urine Detected and Quantified 40 +/- 2.6 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia
Urine Detected and Quantified 31 +/- 11 umol/mmol creatinine Adult (>18 years old) Both Maple syrup urine disease
Urine Detected and Quantified 50.3 +/- 9.9 umol/mmol creatinine Adult (>18 years old) Both Aminoaciduria
Associated Disorders and Diseases
Disease References
Obesity
  • 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 Link_out
      Diabetes mellitus type 2
      • 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 Link_out
          Alzheimer's disease
          • 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 Link_out
              Kidney disease
              • Raj DS, Ouwendyk M, Francoeur R, Pierratos A: Plasma amino acid profile on nocturnal hemodialysis. Blood Purif. 2000;18(2):97-102. Pubmed: 10838467 Link_out
                  Associated OMIM IDs
                  DrugBank ID Not Available
                  DrugBank Metabolite ID Not Available
                  Phenol Explorer Compound ID Not Available
                  Phenol Explorer Metabolite ID Not Available
                  FoodDB ID FDB012119
                  KNApSAcK ID Not Available
                  Chemspider ID 83153 Link_out
                  KEGG Compound ID C01152 Link_out
                  BioCyc ID CPD-1823 Link_out
                  BiGG ID Not Available
                  Wikipedia Link Not Available
                  NuGOwiki Link HMDB00001 Link_out
                  Metagene Link HMDB00001 Link_out
                  METLIN ID 3741 Link_out
                  PubChem Compound 92105 Link_out
                  PDB ID HIC Link_out
                  ChEBI ID 50599 Link_out
                  References
                  Synthesis Reference Jain, 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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  Enzymes
                  Name: Beta-Ala-His dipeptidase
                  Reactions: Not Available
                  Gene Name: CNDP1
                  Uniprot ID: Q96KN2 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Protein arginine N-methyltransferase 3
                  Reactions: Not Available
                  Gene Name: PRMT3
                  Uniprot ID: O60678 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA