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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-11-16 23:20:16 UTC
HMDB IDHMDB0000479
Secondary Accession Numbers
  • HMDB00479
Metabolite Identification
Common Name3-Methylhistidine
Description3-Methylhistidine, also known as 3-MHis or 3MH, belongs to the class of organic compounds known as histidine and derivatives. 3MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. 3-Methylhistidine is also classified as a member of the class of compounds known as L-alpha-amino acids. L-alpha-Amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. 3-Methylhistidine is generated from histidine residues found in proteins. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as pi-methylhistidine) or 3-methylhistidine (3MH; tau-methylhistidine), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine and other histidine-containing peptides such as anserine. In particular, older literature (mostly prior to the year 2000) designated anserine (Npi methylated) as beta-alanyl-N1-methyl-histidine, whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methyl-histidine. As a result, many papers published prior to the year 2000 incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really were referring to 3MH (PMID: 24137022 ). Histidine methylation on the 3- or tau site is mediated by the enzyme known as METTL18. METTL18 is a nuclear methyltransferase protein that contains a functional nuclear localization signal and accumulates in nucleoli. Urinary concentrations of 3-methylhistidine can be used as a biomarker for skeletal muscle protein breakdown in humans who have been subject to muscle injury (PMID: 16079625 ). 3-methylhistidine is formed by the posttranslational methylation of histidine residues of the main myofibrillar proteins actin and myosin. During protein catabolism, 3-methylhistidine is released but cannot be reutilized. Therefore, the plasma concentration and urine excretion of 3-methylhistidine are sensitive markers of myofibrillar protein degradation (PMID: 32235743 ). Approximately 75% of 3-methylhistidine is estimated to originate from skeletal muscle (PMID: 32235743 ). In addition to the degradation of muscle proteins, the 3-methylhistidine level is affected by the degradation of intestinal proteins and meat intake. 3-Methylhistidine exists in all eukaryotes, ranging from yeast to humans. In humans, 3-methylhistidine is involved in methylhistidine metabolism. 3-Methylhistidine has been found to be associated with several diseases such as diabetes mellitus type 2, eosinophilic esophagitis, and kidney disease. The normal concentration of 3-methylhistidine in the urine of healthy adult humans has been detected and quantified in a range of 3.63-69.27 micromoles per millimole (umol/mmol) of creatinine, with most studies reporting the average urinary concentration between 15-20 umol/mmol of creatinine. The average concentration of 3-methylhistidine in human blood plasma has been detected and quantified at 2.85 micromolar (uM) with a range of 0.0-5.9 uM. As a general rule, urinary 1MH is associated with white meat intake (p< 0.001), whereas urinary 3MH is associated with red meat intake (p< 0.001) (PMID: 34091671 ).
Structure
Data?1637094518
Synonyms
ValueSource
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acidChEBI
3-Methyl-L-histidineChEBI
N-pros-Methyl-L-histidineChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoateGenerator
3-N-Methyl-L-histidineHMDB
L-3-MethylhistidineHMDB
N(pros)-Methyl-L-histidineHMDB
N3-Methyl-L-histidineHMDB
3-Methylhistidine hydrideHMDB
3-Methylhistidine dihydrochlorideHMDB
3-MethylhistidineChEBI
Pi methylhistidineHMDB
N(Pi)-methylhistidineHMDB
N Pi-methylhistidineHMDB
Chemical FormulaC7H11N3O2
Average Molecular Weight169.1811
Monoisotopic Molecular Weight169.085126611
IUPAC Name(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional Name3,methylhistidine
CAS Registry Number368-16-1
SMILES
[H][C@](N)(CC1=CN=CN1C)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 KeyJDHILDINMRGULE-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility200 mg/mL at 25 °CBEILSTEIN
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg134.3730932474
[M+H]+MetCCS_train_pos134.08530932474
[M-H]-Not Available137.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000016
[M+H]+Not Available134.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000016
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.93 g/LALOGPS
logP10(-2.9) g/LALOGPS
logP10(-3.4) g/LChemAxon
logS10(-1.4) g/LALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.96 m³·mol⁻¹ChemAxon
Polarizability16.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.42731661259
DarkChem[M-H]-132.69231661259
AllCCS[M+H]+137.93832859911
AllCCS[M-H]-134.37132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methylhistidine[H][C@](N)(CC1=CN=CN1C)C(O)=O2814.7Standard polar33892256
3-Methylhistidine[H][C@](N)(CC1=CN=CN1C)C(O)=O1666.3Standard non polar33892256
3-Methylhistidine[H][C@](N)(CC1=CN=CN1C)C(O)=O1982.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methylhistidine,1TMS,isomer #1CN1C=NC=C1C[C@H](N)C(=O)O[Si](C)(C)C1761.5Semi standard non polar33892256
3-Methylhistidine,1TMS,isomer #2CN1C=NC=C1C[C@H](N[Si](C)(C)C)C(=O)O1862.9Semi standard non polar33892256
3-Methylhistidine,2TMS,isomer #1CN1C=NC=C1C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1861.2Semi standard non polar33892256
3-Methylhistidine,2TMS,isomer #1CN1C=NC=C1C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1797.2Standard non polar33892256
3-Methylhistidine,2TMS,isomer #1CN1C=NC=C1C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2267.1Standard polar33892256
3-Methylhistidine,2TMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1995.6Semi standard non polar33892256
3-Methylhistidine,2TMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1919.9Standard non polar33892256
3-Methylhistidine,2TMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2428.2Standard polar33892256
3-Methylhistidine,3TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2044.1Semi standard non polar33892256
3-Methylhistidine,3TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1954.1Standard non polar33892256
3-Methylhistidine,3TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2157.3Standard polar33892256
3-Methylhistidine,1TBDMS,isomer #1CN1C=NC=C1C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2018.0Semi standard non polar33892256
3-Methylhistidine,1TBDMS,isomer #2CN1C=NC=C1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2110.9Semi standard non polar33892256
3-Methylhistidine,2TBDMS,isomer #1CN1C=NC=C1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2304.8Semi standard non polar33892256
3-Methylhistidine,2TBDMS,isomer #1CN1C=NC=C1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2268.3Standard non polar33892256
3-Methylhistidine,2TBDMS,isomer #1CN1C=NC=C1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2437.1Standard polar33892256
3-Methylhistidine,2TBDMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2437.4Semi standard non polar33892256
3-Methylhistidine,2TBDMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2357.5Standard non polar33892256
3-Methylhistidine,2TBDMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2521.6Standard polar33892256
3-Methylhistidine,3TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2667.8Semi standard non polar33892256
3-Methylhistidine,3TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2596.9Standard non polar33892256
3-Methylhistidine,3TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2457.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-9500000000-ab7d6324146b8775fe502016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistidine GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9400000000-42443c78fdfca9db19262017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistidine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistidine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylhistidine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-2900000000-15f0e43eb0d06e7f3ef32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0002-9200000000-5a1ab4d052e6ba4a76e42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0002-9000000000-c1951c88c84885804fb62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-00di-0900000000-4e0fea0fe9b1142db07b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0592-4900000000-ee1bce969d650e9fcfbe2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0002-9200000000-1ad733cdcfa4db4fe3b92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0002-9000000000-a87ff5cc0642ea3af69c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0002-9000000000-28a73708493f968c2ac62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-9800000000-6565ccf96757ef3bc08f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-014i-0900000000-3cbd02f5b6c4e6e64eb92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-IT , negative-QTOFsplash10-0udi-0900000000-e6ce7548fd6f09e2098f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QTOF , negative-QTOFsplash10-014i-0900000000-3cbd02f5b6c4e6e64eb92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ , positive-QTOFsplash10-00di-0900000000-2d351351f285b21887102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ , positive-QTOFsplash10-0592-4900000000-ee1bce969d650e9fcfbe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ , positive-QTOFsplash10-0002-9200000000-1ad733cdcfa4db4fe3b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ , positive-QTOFsplash10-0002-9000000000-2ed34e7b458d9f8c092f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QQ , positive-QTOFsplash10-0002-9000000000-c1b8a62adc15b80955c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine LC-ESI-QTOF , positive-QTOFsplash10-0002-9800000000-6565ccf96757ef3bc08f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylhistidine 20V, Positive-QTOFsplash10-00di-6900000000-acc4a08855924a8bf5a12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistidine 10V, Positive-QTOFsplash10-00di-0900000000-1ca24429b22e547d10d92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistidine 20V, Positive-QTOFsplash10-00di-1900000000-4cafc4698b6e3649ce7a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistidine 40V, Positive-QTOFsplash10-0002-9300000000-ef0c8b716935df30c5082016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistidine 10V, Negative-QTOFsplash10-014i-1900000000-8a91a6a64bb07285c36d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistidine 20V, Negative-QTOFsplash10-01b9-4900000000-4ad91c6f55caf69120e92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylhistidine 40V, Negative-QTOFsplash10-05di-9300000000-ea67f38340a4b7ef8e112016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.7 (0.0-5.9) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.0 (2.7 - 5.9) uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.82 +/- 2.43 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.00950 +/- 0.0494 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0982 +/- 0.128 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.126 +/- 0.139 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.134 +/- 0.110 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified27.68 +/- 28.12 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified32.79 +/- 20.35 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified39.57 +/- 15.83 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified8.71-29.41 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified5.26 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified39.57 +/- 23.74 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified5.8-50 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified5.32-29.64 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified7.92-27.83 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified9.95-39.59 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified5.4-35 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified69.27 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified16.5 (2.8-59.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified9.73-37.33 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified12.5 +/- 4.2 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified44.944 +/- 41.318 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified6.33-35.75 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified42.76 +/- 22.84 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified17.977 +/- 5.902 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified18.191 +/- 7.0323 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified15.806 +/- 5.404 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified13.556 +/- 2.487 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified18.203 +/- 6.512 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified17.705 +/- 6.00349 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified16.0206 +/- 4.895 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified17.0268 +/- 1.572 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.0 +/- 10.4 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified23.7 +/- 18.6 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified50.7 (12.9) uMAdult (>18 years old)FemaleEarly preeclampsia details
BloodDetected and Quantified50.0 (14.6) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified5.16 +/- 1.27 uMElderly (>65 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified2.48 +/- 1.58 uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified24.0 +/- 1.7 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease details
UrineDetected and Quantified11.6 +/- 6.6 umol/mmol creatinineAdult (>18 years old)Not SpecifiedDiabetes mellitus details
UrineDetected and Quantified16.0 +/- 9.0 umol/mmol creatinineAdult (>18 years old)Not SpecifiedObesity details
UrineDetected and Quantified57.778 +/- 73.153 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified44.5 +/- 1.3 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia details
Associated Disorders and Diseases
Disease References
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 ]
Early preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
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 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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 ]
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 ]
Propionic acidemia
  1. Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB093613
KNApSAcK IDNot Available
Chemspider ID58494
KEGG Compound IDC01152
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylhistidine
METLIN ID5466
PubChem Compound64969
PDB IDNot Available
ChEBI ID27596
Food Biomarker OntologyNot Available
VMH ID3MHIS
MarkerDB IDMDB00000170
Good Scents IDNot Available
References
Synthesis ReferenceOhba, 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. 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 ]
  2. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. Young VR, Munro HN: Ntau-methylhistidine (3-methylhistidine) and muscle protein turnover: an overview. Fed Proc. 1978 Jul;37(9):2291-300. [PubMed:350635 ]
  22. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  23. Boldyrev AA, Aldini G, Derave W: Physiology and pathophysiology of carnosine. Physiol Rev. 2013 Oct;93(4):1803-45. doi: 10.1152/physrev.00039.2012. [PubMed:24137022 ]
  24. Chinkes DL: Methods for measuring tissue protein breakdown rate in vivo. Curr Opin Clin Nutr Metab Care. 2005 Sep;8(5):534-7. doi: 10.1097/01.mco.0000170754.25372.37. [PubMed:16079625 ]
  25. Holecek M: Histidine in Health and Disease: Metabolism, Physiological Importance, and Use as a Supplement. Nutrients. 2020 Mar 22;12(3). pii: nu12030848. doi: 10.3390/nu12030848. [PubMed:32235743 ]
  26. Said MY, Rodriguez-Nino A, Post A, Schutten JC, Kieneker LM, Gomes-Neto AW, van Londen M, Oste MC, Borgonjen-van den Berg KJ, Nolte IM, van den Berg E, de Blaauw P, van der Krogt J, Heiner-Fokkema MR, Navis G, Yard BA, Bakker SJ: Meat intake and risk of mortality and graft failure in kidney transplant recipients. Am J Clin Nutr. 2021 Jun 5. pii: 6294068. doi: 10.1093/ajcn/nqab185. [PubMed:34091671 ]

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
General function:
Involved in catalytic activity
Specific function:
Catalyzes the synthesis of carnosine and homocarnosine. Carnosine is synthesized more efficiently than homocarnosine.
Gene Name:
CARNS1
Uniprot ID:
A5YM72
Molecular weight:
101318.725
Reactions
Adenosine triphosphate + 3-Methylhistidine + beta-Alanine → Adenosine monophosphate + Pyrophosphate + Anserinedetails
General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
Reactions
L-Histidine + S-Adenosylmethionine → 3-Methylhistidine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Reactions
L-Histidine + S-Adenosylmethionine → 3-Methylhistidine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Reactions
L-Histidine + S-Adenosylmethionine → 3-Methylhistidine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available
Reactions
L-Histidine + S-Adenosylmethionine → 3-Methylhistidine + S-Adenosylhomocysteinedetails