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Human Metabolome Database Version 3.5

Showing metabocard for 1-Methylhistidine (HMDB00001)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (2)

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2005-11-16 08:48:42 -0700
Update Date	2013-02-08 17:07:43 -0700
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	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	1 Methylhistidine 1-Methyl histidine 1-Methyl-Histidine 1-Methyl-L-histidine 1-MHis 1-N-Methyl-L-histidine L-1-Methylhistidine N1-Methyl-L-histidine 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	4-methyl-histidine
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
Normal Concentrations
	Biofluid Status Value Age Sex Condition Comments Blood Detected and Quantified 7.7 +/- 1.9 uM Adult (>18 years old) Both Normal Not Available Blood Detected and Quantified 14.4 +/- 2.3 uM Adult (>18 years old) Both Normal Not Available Blood Detected and Quantified 19.6 +/- 2.6 uM Adult (>18 years old) Both Normal Not Available Blood Detected and Quantified 12.7 +/- 2.9 uM Adult (>18 years old) Both Normal Not Available Blood Detected and Quantified 20.2 +/- 4.0 uM Adult (>18 years old) Both Normal Not Available Blood Detected and Quantified 9.1 +/- 7.2 uM Children (1-13 year old) Not Specified Normal Not Available Blood Detected and Quantified 4.0 +/- 8.0 uM Adult (>18 years old) Both Normal Not Available Cerebrospinal Fluid (CSF) Detected and Quantified 4.0 +/- 1.74 uM Adult (>18 years old) Both Normal Not Available Saliva Detected and Quantified 26.34 uM Adult (>18 years old) Both Normal Not Available Urine Detected and not Quantified Not Applicable Not Available Male Normal Not Available Urine Detected and Quantified 17.74-153.77 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 8.3 (2.4-28.4) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR Urine Detected and Quantified 30.0 +/- 43.0 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.0019 - 0.0038 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 4.6 +/- 2.7 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available Urine Detected and Quantified 2.3 +/- 5.1 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available Urine Detected and Quantified 46.1 +/- 53.5 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available Urine Detected and Quantified 15.9 +/- 19.5 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available Urine Detected and Quantified 28.1 +/- 31.8 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available Urine Detected and Quantified 1.3 +/- 2.76 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available Urine Detected and Quantified 45.5 +/- 41.6 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available Urine Detected and Quantified 33.6 +/- 36.4 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Abnormal Concentrations
	Biofluid Status Value Age Sex Condition Comments Blood Detected and Quantified 28.8 +/- 18.2 uM Adult (>18 years old) Both Kidney disease Patients with chronic renal failure on... Blood Detected and Quantified 83.1 +/- 21.7 uM Adult (>18 years old) Both Kidney disease Patients with chronic renal failure on... Blood Detected and Quantified 10.66 +/- 2.68 uM Elderly (>65 years old) Both Alzheimer's disease Probable Alzheimer's disease Cerebrospinal Fluid (CSF) Detected and Quantified 2.6 +/- 1.13 uM Adult (>18 years old) Both Alzheimer's disease Not Available Urine Detected and Quantified 10.9 +/- 10.1 umol/mmol creatinine Adult (>18 years old) Both Obesity Not Available Urine Detected and Quantified 17.5 +/- 25.7 umol/mmol creatinine Adult (>18 years old) Both Diabetes Not Available Urine Detected and Quantified 0.0031 - 0.0042 umol/mmol creatinine Adult (>18 years old) Both ADPKD Not Available Urine Detected and Quantified 15.7 +/- 4.04 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease Probable Alzheimer's disease Urine Detected and Quantified 40 +/- 2.6 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia Not Available Urine Detected and Quantified 31 +/- 11 umol/mmol creatinine Adult (>18 years old) Both Maple syrup urine disease Not Available Urine Detected and Quantified 50.3 +/- 9.9 umol/mmol creatinine Adult (>18 years old) Both Aminoaciduria Not Available
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 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 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 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
Associated OMIM IDs	104300 (Alzheimer's disease) 125853 (Diabetes mellitus type 2) 601665 (Obesity)
External Links
DrugBank 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
KEGG Compound ID	C01152
BioCyc ID	CPD-1823
BiGG ID	Not Available
Wikipedia Link	Not Available
NuGOwiki Link	HMDB00001
Metagene Link	HMDB00001
METLIN ID	3741
PubChem Compound	92105
PDB ID	HIC
ChEBI ID	50599
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	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 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 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 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 Vranic L, Granic P, Rajic Z: Basic amino acid in the pathogenesis of caries. Acta Stomatol Croat. 1991;25(2):71-6. Pubmed: 1819935 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 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 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 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 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 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 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

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Enzymes
Name: Beta-Ala-His dipeptidase Reactions: Gene Name: CNDP1 Uniprot ID: Q96KN2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Protein arginine N-methyltransferase 3 Reactions: Gene Name: PRMT3 Uniprot ID: O60678 Protein Sequence: FASTA Gene Sequence: FASTA

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