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Human Metabolome Database Version 3.5

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Showing metabocard for 3-Methylhistidine (HMDB00479)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:40 -0700
HMDB ID HMDB00479
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Methylhistidine
Description 3-Methylhistidine is a product of peptide bond synthesis and methylation of actin and myosin. The measurement of 3-Methylhistidine provides an index of the rate of muscle protein breakdown.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoate
  2. (2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
  3. 3-Methyl-L-histidine
  4. 3-Methylhistidine
  5. 3-N-Methyl-L-histidine
  6. L-3-Methylhistidine
  7. N(Pai)-Methyl-L-histidine
  8. N(Pi)-methyl-L-histidine
  9. N(Pros)-methyl-L-histidine
  10. N3-Methyl-L-histidine
  11. Pi-Methyl-L-histidine
  12. Tau-Methyl-L-histidine
  13. Tau-methylhistidine
Chemical Formula C7H11N3O2
Average Molecular Weight 169.1811
Monoisotopic Molecular Weight 169.085126611
IUPAC Name (2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional IUPAC Name 3-methylhistidine
CAS Registry Number 368-16-1
SMILES CN1C=NC=C1C[C@H](N)C(O)=O
InChI Identifier InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
InChI Key JDHILDINMRGULE-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 200 mg/mL at 25 °C BEILSTEIN
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 6.93 g/L ALOGPS
LogP -2.89 ALOGPS
LogP -3.4 ChemAxon
LogS -1.39 ALOGPS
pKa (strongest acidic) 1.96 ChemAxon
pKa (strongest basic) 9.43 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 81.14 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 42.96 ChemAxon
Polarizability 16.58 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Prostate
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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2.7 (0.0-5.9) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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3.0 (2.7 - 5.9) uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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3.82 +/- 2.43 uM Adult (>18 years old) Not Specified Normal Not Available
Urine Detected and Quantified
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5.26 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.0012 - 0.0286 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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69.27 umol/mmol creatinine Adult (>18 years old) Male Normal Based on one measurement
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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16.5 (2.8-59.8) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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12.5 +/- 4.2 umol/mmol creatinine Adult (>18 years old) Not Specified Normal Not Available
Urine Detected and Quantified
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42.76 +/- 22.84 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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13.0 +/- 10.4 uM Adult (>18 years old) Both Kidney disease Patients with chronic renal failure on...
Blood Detected and Quantified
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23.7 +/- 18.6 uM Adult (>18 years old) Both Kidney disease Patients with chronic renal failure on...
Blood Detected and Quantified
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5.16 +/- 1.27 uM Elderly (>65 years old) Both Alzheimer's disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.48 +/- 1.58 uM Adult (>18 years old) Not Specified Alzheimer's disease Not Available
Urine Detected and Quantified
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0.0013 - 0.0303 umol/mmol creatinine Adult (>18 years old) Both ADPKD Not Available
Urine Detected and Quantified
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24.0 +/- 1.7 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease Not Available
Urine Detected and Quantified
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11.6 +/- 6.6 umol/mmol creatinine Adult (>18 years old) Not Specified Diabetes mellitus Not Available
Urine Detected and Quantified
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16.0 +/- 9.0 umol/mmol creatinine Adult (>18 years old) Not Specified Obesity Not Available
Urine Detected and Quantified
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44.5 +/- 1.3 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia Not Available
Associated Disorders and Diseases
Disease References
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
    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
      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
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB021798
          KNApSAcK ID Not Available
          Chemspider ID 58494 Link_out
          KEGG Compound ID C01152 Link_out
          BioCyc ID Not Available
          BiGG ID Not Available
          Wikipedia Link Not Available
          NuGOwiki Link HMDB00479 Link_out
          Metagene Link HMDB00479 Link_out
          METLIN ID 5466 Link_out
          PubChem Compound 64969 Link_out
          PDB ID MHS Link_out
          ChEBI ID 27596 Link_out
          References
          Synthesis Reference Ohba, Masashi; Mukaihira, Takafumi; Fujii, Tozo. Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines. Chemical & Pharmaceutical Bulletin (1994), 42(9), 1784-90.
          Material Safety Data Sheet (MSDS) Download (PDF)
          General References
          1. Bucciante G, Mencini A, Boninsegna A, Branca D, Scutari A, Scutari G: 3-Methylhistidine urinary excretion as an index of skeletal muscle protein metabolism: reference values. G Clin Med. 1985 Nov-Dec;66(11-12):451-8. Pubmed: 3835089 Link_out
          2. Schmitz JE: [Effect of metabolism-oriented substrate administration on energy and protein metabolism in polytraumatized artificial respiration patients] Infusionsther Klin Ernahr. 1984 Aug;11(4):205-18. Pubmed: 6434422 Link_out
          3. McKeran RO, Halliday D, Purkiss P: Comparison of human myofibrillar protein catabolic rate derived from 3-methylhistidine excretion with synthetic rate from muscle biopsies during L-[alpha-15N]lysine infusion. Clin Sci Mol Med. 1978 May;54(5):471-5. Pubmed: 750147 Link_out
          4. Teahon K, Rideout JM: A sensitive and specific high performance liquid chromatographic assay for imidazole dipeptides and 3-methylhistidine in human muscle biopsies, serum and urine. Biomed Chromatogr. 1992 Jan-Feb;6(1):16-9. Pubmed: 1600369 Link_out
          5. Adlerberth A, Jagenburg R, Lindstedt G, Stenstrom G, Hasselgren PO: Effects of thyroid hormone and beta-adrenoceptor blocking agents on urinary excretion of 3-methylhistidine and plasma amino acids in man. Eur J Clin Invest. 1986 Aug;16(4):316-20. Pubmed: 3093243 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. Wang Z, Deurenberg P, Matthews DE, Heymsfield SB: Urinary 3-methylhistidine excretion: association with total body skeletal muscle mass by computerized axial tomography. JPEN J Parenter Enteral Nutr. 1998 Mar-Apr;22(2):82-6. Pubmed: 9527964 Link_out
          8. Nygren J, Thorell A, Brismar K, Essen P, Wernerman J, McNurlan MA, Garlick PJ, Ljungqvist O: Glucose flux is normalized by compensatory hyperinsulinaemia in growth hormone-induced insulin resistance in healthy subjects, while skeletal muscle protein synthesis remains unchanged. Clin Sci (Lond). 2002 Apr;102(4):457-64. Pubmed: 11914108 Link_out
          9. Elia M, Carter A, Bacon S, Winearls CG, Smith R: Clinical usefulness of urinary 3-methylhistidine excretion in indicating muscle protein breakdown. Br Med J (Clin Res Ed). 1981 Jan 31;282(6261):351-4. Pubmed: 6780020 Link_out
          10. Rathmacher JA, Flakoll PJ, Nissen SL: A compartmental model of 3-methylhistidine metabolism in humans. Am J Physiol. 1995 Jul;269(1 Pt 1):E193-8. Pubmed: 7631776 Link_out
          11. Lunyong VE, Friedman Z: Myofibrillar protein degradation in premature infants with respiratory distress as assessed by 3-methylhistidine and creatinine excretions. Am J Clin Nutr. 1982 Sep;36(3):485-91. Pubmed: 7113954 Link_out
          12. Buchholz-Wimmer GB, Wimmer W, Herbertz L, Reinauer H: [3-Methylhistidine as a parameter for the determination of muscle proteolysis in the post-stress syndrome and in diabetes mellitus] Infusionsther Klin Ernahr. 1984 Jun;11(3):168-74. Pubmed: 6434416 Link_out
          13. Vesali RF, Klaude M, Thunblad L, Rooyackers OE, Wernerman J: Contractile protein breakdown in human leg skeletal muscle as estimated by [2H3]-3-methylhistidine: a new method. Metabolism. 2004 Aug;53(8):1076-80. Pubmed: 15281022 Link_out
          14. Bird SP, Tarpenning KM, Marino FE: Independent and combined effects of liquid carbohydrate/essential amino acid ingestion on hormonal and muscular adaptations following resistance training in untrained men. Eur J Appl Physiol. 2006 May;97(2):225-38. Epub 2006 Mar 24. Pubmed: 16456674 Link_out
          15. Lamisse F, May MA, Couet C, Constans T, Bacq Y, Delarue J, Lamagnere JP, Colombat P, Garrigue MA: [Changes in nutritional status at the initial phase of treatment of cancers and malignant hemopathies] Rev Med Interne. 1987 May-Jun;8(3):257-61. Pubmed: 3616232 Link_out
          16. Neuhauser M, Bergstrom J, Chao L, Holmstrom J, Nordlund L, Vinnars E, Furst P: Urinary excretion of 3-methylhistidine as an index of muscle protein catabolism in postoperative trauma: the effect of parenteral nutrition. Metabolism. 1980 Dec;29(12):1206-13. Pubmed: 6779092 Link_out
          17. Emery PW, Rennie MJ: Elimination by formaldehyde of interference with 3-methylhistidine determination: application of the method to the study of muscle protein degradation. Anal Biochem. 1982 Oct;126(1):67-73. Pubmed: 7181118 Link_out
          18. Tomas FM, Ballard FJ, Pope LM: Age-dependent changes in the rate of myofibrillar protein degradation in humans as assessed by 3-methylhistidine and creatinine excretion. Clin Sci (Lond). 1979 Apr;56(4):341-6. Pubmed: 477219 Link_out
          19. Long CL, Dillard DR, Bodzin JH, Geiger JW, Blakemore WS: Validity of 3-methylhistidine excretion as an indicator of skeletal muscle protein breakdown in humans. Metabolism. 1988 Sep;37(9):844-9. Pubmed: 3138511 Link_out
          20. Young VR, Munro HN: Ntau-methylhistidine (3-methylhistidine) and muscle protein turnover: an overview. Fed Proc. 1978 Jul;37(9):2291-300. Pubmed: 350635 Link_out
          21. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
          Enzymes
          Name: Beta-Ala-His dipeptidase
          Reactions:
          • Preferential hydrolysis of the beta-Ala!His dipeptide (carnosine), and also anserine, Xaa!His dipeptides and other dipeptides including homocarnosine [RN:R01166 R03288] ALL_REAC R01166 R03288 COFACTOR Citrate [CPD:C00158]
          • Cadmium [CPD:C01413]
          Gene Name: CNDP1
          Uniprot ID: Q96KN2 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA