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Record Information
Version1.0
Creation Date2016-07-13 19:22:06 UTC
Update Date2021-04-30 20:57:56 UTC
LmdbLMDB00001
Secondary Accession NumbersNone
Metabolite Identification
Common Name1-Methylhistidine
Description1-Methylhistidine, also known as 1-mhis, 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. 1-Methylhistidine exists in all living organisms, ranging from bacteria to humans. In humans, 1-methylhistidine is involved in the histidine metabolism pathway. 1-Methylhistidine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 1-methylhistidine a potential biomarker for the consumption of these foods. 1-Methylhistidine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 1-Methylhistidine, with regard to humans, has been found to be associated with several diseases such as alzheimer's disease, eosinophilic esophagitis, and diabetes mellitus type 2; 1-methylhistidine has also been linked to several inborn metabolic disorders including maple syrup urine disease and propionic acidemia. Based on a literature review a significant number of articles have been published on 1-Methylhistidine.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acidChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoateGenerator
1 MethylhistidineHMDB
1-Methyl histidineHMDB
1-Methyl-histidineHMDB
1-Methyl-L-histidineHMDB
1-MHisHMDB
1-N-Methyl-L-histidineHMDB
L-1-MethylhistidineHMDB
N1-Methyl-L-histidineHMDB
1-Methylhistidine dihydrochlorideHMDB
1-MethylhistidineChEBI
Tau methylhistidineHMDB
N(Tau)-methylhistidineHMDB
Tau-methyl-L-histidineHMDB
N Tau-methylhistidineHMDB
Chemical FormulaC7H11N3O2
Average Molecular Weight169.1811
Monoisotopic Molecular Weight169.085126611
IUPAC Name2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid hydrate
Traditional Name4-methyl-histidine hydrate
CAS Registry Number332-80-9
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 KeyBRMWTNUJHUMWMS-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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-3.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.39 m³·mol⁻¹ChemAxon
Polarizability17.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-9610000000-d0147d3e28362f91174aSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gbd-4941000000-cee19577c72eecd95aecSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-9610000000-d0147d3e28362f91174aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gbd-4941000000-cee19577c72eecd95aecSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-9500000000-e50450f2dc8a5d4b3655Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9310000000-d6f7eb07e6f5ecb74263Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-037d24a7d65676b7e356Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0900000000-03e99316bd6c098f5d11Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00ea-9800000000-a33c82a1c91f56d372feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-695bcc2d0a01df2d7521Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-4eea9cf6f12f18d06f98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05us-9300000000-072d6fe7a7a03cd7390bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-57f1e30ae8b606ea5f5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-5900000000-ff71b6d300a9ee595b3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adj-9300000000-e045823003ab541d5b1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8b15275d24e410674982Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0592-5900000000-9af09354b313cccd21aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5a-9500000000-6fff2b3f74fb49f4b389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a2577f99286255ceb6f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-2900000000-39dfca8cd6f4c3e15a96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9100000000-de4522e3df03361bc39aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected and Quantified17 +/- 1-19+/-2 uMNot AvailablePorcine details
PlasmaDetected and Quantified25 +/- 1-24+/-4 uMNot AvailablePorcine details
PlasmaDetected and Quantified29 +/- 6-20+/-2 uMNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified61 uMNot AvailablePorcine details
SerumDetected and Quantified72.644 uMNot AvailablePorcine details
SerumDetected and Quantified50.124 uMNot AvailablePorcine details
SerumDetected and Quantified62.182 uMNot AvailablePorcine details
SerumDetected and Quantified83.7017 +/- 26.5027 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified78.3264 +/- 20.9583 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified64.3864 +/- 25.6295 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified65.9809 +/- 31.5215 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified38.85 +/- 17.67 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified76.8997 +/- 14.1496 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • Lucia Pappalardo,...
details
SerumDetected and Quantified60.5854 +/- 17.4741 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified78.8319 +/- 26.1811 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified84.7309 +/- 26.0394 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified69.0192 +/- 19.186 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified67.678 +/- 25.7615 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified76.5402 +/- 29.5597 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified85.9343 +/- 29.1249 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified76.1201 +/- 20.9519 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified71.1698 +/- 32.2155 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified71.8906 +/- 34.956 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified84.9698 +/- 34.2423 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified88.3722 +/- 21.1699 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified66.9318 +/- 18.2983 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified59.3064 +/- 21.9801 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified59.0153 +/- 20.9635 uM
Normal
Ovine
    • Goldansaz et al.,...
details
DrugBank IDDB04151
HMDB IDHMDB0000001
FooDB IDFDB093588
Phenol Explorer IDNot Available
KNApSAcK IDC00052105
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3741
PDB IDNot Available
Wikipedia LinkMethylhistidine
Chemspider ID83153
ChEBI ID50599
PubChem Compound ID92105
Kegg Compound IDC01152
YMDB IDNot Available
ECMDB IDECMDB24006
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available