Human Metabolome Database Version 3.5

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 | PDB | 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 Reference
Blood Detected and Quantified
2.7 (0.0-5.9) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
3.0 (2.7 - 5.9) uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
3.82 +/- 2.43 uM Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
5.26 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0012 - 0.0286 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
69.27 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
  • Shaykhutdino...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
16.5 (2.8-59.8) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
12.5 +/- 4.2 umol/mmol creatinine Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
42.76 +/- 22.84 umol/mmol creatinine Infant (0-1 year old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 13.0 +/- 10.4 uM Adult (>18 years old) Both Comment Kidney disease
Blood Detected and Quantified 23.7 +/- 18.6 uM Adult (>18 years old) Both Comment Kidney disease
Blood Detected and Quantified 5.16 +/- 1.27 uM Elderly (>65 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 2.48 +/- 1.58 uM Adult (>18 years old) Not Specified Alzheimer's disease
Urine Detected and Quantified 0.0013 - 0.0303 umol/mmol creatinine Adult (>18 years old) Both ADPKD
Urine Detected and Quantified 24.0 +/- 1.7 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease
Urine Detected and Quantified 11.6 +/- 6.6 umol/mmol creatinine Adult (>18 years old) Not Specified Diabetes mellitus
Urine Detected and Quantified 16.0 +/- 9.0 umol/mmol creatinine Adult (>18 years old) Not Specified Obesity
Urine Detected and Quantified 44.5 +/- 1.3 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia
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
                  DrugBank Metabolite 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: Not Available
                  Gene Name: CNDP1
                  Uniprot ID: Q96KN2 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Carnosine synthase 1
                  Reactions:
                  Adenosine triphosphate + 3-Methylhistidine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + Anserine details
                  Gene Name: CARNS1
                  Uniprot ID: A5YM72 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: HemK methyltransferase family member 1
                  Reactions:
                  L-Histidine + S-Adenosylmethionine unknown 3-Methylhistidine + S-Adenosylhomocysteine details
                  Gene Name: HEMK1
                  Uniprot ID: Q9Y5R4 Link_out
                  Name: Methyltransferase-like protein 2B
                  Reactions:
                  L-Histidine + S-Adenosylmethionine unknown 3-Methylhistidine + S-Adenosylhomocysteine details
                  Gene Name: METTL2B
                  Uniprot ID: Q6P1Q9 Link_out
                  Name: Methyltransferase-like protein 6
                  Reactions:
                  L-Histidine + S-Adenosylmethionine unknown 3-Methylhistidine + S-Adenosylhomocysteine details
                  Gene Name: METTL6
                  Uniprot ID: Q8TCB7 Link_out
                  Name: Uncharacterized methyltransferase WBSCR22
                  Reactions:
                  L-Histidine + S-Adenosylmethionine unknown 3-Methylhistidine + S-Adenosylhomocysteine details
                  Gene Name: WBSCR22
                  Uniprot ID: O43709 Link_out